


Super Naturally Gay

by DontFightTheGay



Category: Supernatural
Genre: Bad Parent John Winchester, Castiel is So Done with Dean Winchester, Dean Winchester Needs a Hug, Dean Winchester is Jack Kline's Parent, F/F, F/M, Homophobia, Internalized Homophobia, Jack Needs a Hug, John Abuses Dean, John Winchester's A+ Parenting, M/M, Minor Benny Lafitte/Dean Winchester, Minor Jessica Moore/Sam Winchester, No Proofreading!, Quote: Y yo a ti Cas | Me too (Supernatural), Sam has good intentions, Self-Discovery, Self-Harm, Sexism, Shout-Out to Kate, This is for my friend Kate, Trans Character, Trans Dean Winchester, but he really is oblivious, idk what to tag i'm literally so bad at ao3, thats sarcastic, we die like the rats we are, you can't change my mind on this fuck you
Language: English
Status: In-Progress
Published: 2020-12-22
Updated: 2021-01-08
Packaged: 2021-03-10 23:13:01
Rating: Mature
Warnings: Graphic Depictions Of Violence, Rape/Non-Con, Underage
Chapters: 7
Words: 24,823
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28245222
Author URL: https://archiveofourown.org/users/DontFightTheGay/pseuds/DontFightTheGay
Summary: Dean Winchester, formerly Mary Deanna Winchester, doesn't understand why bad things happen to him. Traumatized because of John Winchester, Dean fakes his death so he can escape John's wrath after Sam applies to Stanford. He takes the Impala and high-tails it out of there only to meet Charlie Bradbury. This story answers the age-long question of what happens when a lesbian and a bisexual walk into a bar.Basically a retelling of Supernatural but I only reference the episodes because I don't hate myself enough to rewrite exact episodes. Just pretend each chapter or part is a season. I'll try putting it in the chapter names but no promises that I will remember. This will be done when it gets done. I forgot I have a job lmao
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Comments: 20
Kudos: 66





	1. Did I forget to turn off the stove?

**Author's Note:**

  * For [Kate : )](https://archiveofourown.org/gifts?recipient=Kate+%3A+%29).



> I gave my friend a note that had a summary of what I wanted to write and to not disappoint her, I'm writing this as her Christmas present. Please comment "Merry Christmas, Kate" thanks <3
> 
> K

November 2, 1983

Her heart is going to explode. She knows it is about four seconds away from exploding and she still has Sam in her arms. Is Sam going to die because her heart will explode? Mary Deanna Winchester turns to look at her house, smoke and flames coming out of the top floor windows where she remembered her mom sat singing to her not even five hours ago. 

“Daddy? Mommy?” She yells toward the house. Mary takes a step toward the door and hopes to see her parents coming out. Sam let out a very long wail at the motion and Mary shifts him in her arms. “Sammy, it’s okay. Mommy and daddy are coming just wait. They’re both going to come and get you and mommy will sing her special song for us. Do you remember the song Sammy?”

Sam continues to cry loudly. She looks towards the front door again and sees her dad crawl out before a loud bang sounds behind him. 

“Daddy? Where’s mommy?” Mary asks as she runs towards him. John Winchester coughs loudly before trying to stand up. 

“Not- she’s not- Mary…you’re the new mommy, sweetie…your mom, she’s-” John coughs again and rests his head against the ground. Mary looks towards the fire trying to see where her mom is. 

Just as she takes a step towards the door, one of their neighbors comes by to help her daddy stand. Mrs. Patty squats down next to Mary to take Sam. 

“Mary, dear, I’ll take Sam. Why don’t you go with Mr. Gill and get some water?” Mrs. Patty looks at her husband who nods and holds out his hand. Mary holds Sam a little tighter. “Mary, please, your daddy needs some water. Why don’t you go get him some?”

At this, Mary finally releases Sam to her and takes Mr. Gill’s hand. “Will mommy also need water?”

The two adults share a glance. Gill leads Mary towards their house across the street. “She might need water if she gets out. Let’s make sure we get enough.”

“Okay, Mr. Gill.” She whispers, turning to look back to where her dad was being helped up by some EMTs. She hears sirens as soon as she steps through the front door of the Robertson's house. 

Mary sits down at their kitchen table while Gill grabs a few glasses and puts them in a bag. He grabs the pitcher from the fridge and sets both on the table in front of Mary. 

“Mary? How are you doing?” Gill sits across from her. 

“I’m fine, Mr. Gill.” Mary looks down to her hands. Has her mom gotten out of the house yet? “Do you know if my mommy came out yet?”

Gill looks down and runs a hand through his grey hair before he speaks. “I don’t know, sweetie. She...well, she might not come out.”

Mary looks up at him, her breathing is hard and she feels really tired. “Don’t be silly, she has to.” 

Gill smiles at her, tears starting to form in his eyes. “Okay, sweetie. Let’s go get this water to your family.” He stands up and grabs the bag and pitcher. 

Mary watches him leave, her heart seems to disappear as she looks out the window to see firefighters come out of their truck.


	2. AKA the chapter in which a lot of triggering stuff happens

**Summary for the Chapter:**

> TW to abuse, rape, homophobic language, transphobic implications, and an overall bad time. 
> 
> also please comment what I should tell Kate when I send her the link to this. It should be like idk 10 chapters or so and I am starting chapter four right now

***Very Triggering, this is your last warning. Don't worry, everything here and more will be alluded to in later chapters : ) ***

December 3, 1984 

Mary doesn’t understand why she had to clean the motel room they were staying in. The motel had maids who would clean the room, so why did she have to do it? 

“You almost done, Mare?” John calls from the bed. Mary looks up from the bathtub she was cleaning. 

“Almost, daddy.” She looks down and continues to scrub. 

“Alright, well, hurry up and heat up dinner.” John is looking through a few local newspapers trying to find anything about the supernatural. As he scans the paper from Sioux Falls, he finds an obituary about a guy who was burned to death. That sounds like what happened to Mary, John thinks. He digs around his duffle bag for a map and finds a route to the town. If they leave tomorrow morning, they would be able to reach the town by noon. 

“Mary? After dinner, pack our bags. We’re heading out tomorrow.”

Mary peeks her head out of the bathroom. “Are you going on a hunt?”

John turns his eyes toward her. Her resemblance to her namesake is almost uncanny. The only difference is how young she is. “Yes.”

“Can I come with you? Please?”

John sighs. “Mary, we talked about this. You have to learn how to cook and clean before I even think of teaching you how to hunt.” Like he would ever teach her. She’s a woman, she has to take care of the home because Mary is gone. 

“Okay, daddy. I can’t wait to go with you on a hunt.”

“Okay, Mare. Now remember, we’re leaving very early tomorrow so I need the bags packed and ready to go before then. I’ll make Sam a bottle but when I’m done, I expect you to be out here heating up dinner, okay?”

“Okay, daddy.”

“Call me sir when I ask you to do something, Mary.”

“Yes, sir.”

December 5, 1984

Bobby Singer didn’t want kids. He remembers the fight he had with Karen about it a few days before she died.

“I break everything I touch!’ He had yelled. 

Karen had tears in her eyes and after he said it, the tears dripped down her face. “You haven’t broken me, yet, Robbie.” She turned to leave, but Bobby caught her arm. 

“Karen, please-”

“No, Robert,” She looked over her shoulder at him. “I just need some time alone. I’ll be back.”

Bobby shakes his head. She died almost ten years ago. He looks at the sleeping baby in the little girl’s arms and sighs before standing up.

“I’ll cook us up some lunch, kids. Your daddy should be back soon.” 

Mary started to get up. “I’ll make us food, Mr. Singer.”

“Nah, Mary, it’s okay.” He smiles. “I’ll whip us up some mac and cheese or something. Does that sound good?”

Mary looked at Sam. “Can I watch?” She looks up at Bobby. “I need to learn how to cook real food for my daddy and Sam. I don’t know how to make mac and cheese yet.”

Bobby pauses in the doorway to the kitchen. “John has you cooking in the kitchen?”

“Yeah, he says I gotta learn how to cook before I can learn about hunting. I asked him.” She smiles at Bobby as she places Sam in the makeshift crib. “So, is it okay if I watch you make it?”

Bobby looks out the window. Would Karen want her daughter to learn to cook at five years old? He looks back at Mary and her green eyes. He holds out his hand for her to take. “Okay, Mary. You can watch, but I don't know how helpful watching me cook. My wife, Karen, cooks way better than me.”

Mary smiles wider and takes his hand. “Thank you Mr. Singer.”

“Call me Bobby, kid. Mr. Singer makes me sound so old.” He lets a smile escape the corner of his mouth as he pulls up a chair for Mary to stand on while he cooks. 

John comes back covered in blood. Rufus steps in after him, equally covered, and makes his way to Bobby as John goes to shower off the blood. “He’ll make a good hunter, Bobby. He has the heart and killed the bastard, but he seems to learn fast.”

Bobby nods. Rufus gives his shoulder a pat before heading off to the other shower to clean off. Bobby walks back to the living room and checks on Sam and Mary. Both are asleep, Mary tucked into the couch cushions and Sam in the crib. He turns his head towards the stairs. 

If John keeps hunting, these kids will be here more often. Bobby thinks about how John ignored his kids and went straight to shower. If he had kids, they would be the first thing he checked. Bobby walks to the kitchen to make a drink. He’ll stay here and wait to see if John ever checks up on Mary and Sam.

John never comes downstairs.

November 2, 1986

John left Sam with Bobby. 

“I’m gonna take Mary on a hunt with me.” 

Bobby looks up from his beer. “You sure that’s a good idea? She’s six years old.” 

John laughs. “It’s not going to be a real hunt. I’m going to have her research stuff and when she’s asleep, I’ll pretend to hunt it down.”

Bobby scoffs. “You sure that’s a good idea? She’ll be right angry with you when she figures out it’s fake.”

John’s arms cross as he shifts his feet. “She won’t figure it out. She’s a good kid, but not that smart.” 

Bobby’s brows furrow. “Are we talking about the same Mary? Your kid loves to learn.”

John laughed. “Mary may act like she likes to learn, but she doesn’t. She likes to cook and clean, which is better, anyway. At least then she’ll be able to make a man happy later on.”

John moves to the back of the Impala and starts loading the car. Bobby is shocked. Did John not have any faith in his little girl’s abilities? Bobby storms back into his house to find Mary in the kitchen packing up a few sandwiches. 

“Mary? Are you sure you want to go on this hunt? It’s okay to wait another year until you’re ready, you know.” 

Mary zips up the bag before looking at Bobby. “I want to go. It’s my chance to prove to my dad that I can be a man.”

“You don’t need to be a man, Mary.” He walks over to her and squeezes her shoulder. “You just have to be yourself. Why do you need to prove yourself to your daddy?”

Mary scoffs. “No offense, Mr. Bobby, but I don’t think you would understand.”

Bobby steers Mary towards the kitchen table. “Then can you try to explain it for me, kid?”

“It’s like…” Mary sits down with a sigh. “It’s like I’m not real. Like I don't feel like myself. If I prove to my dad I can hunt, then maybe I’ll find my place.”

Bobby stares at her. 

“See?” She says, grabbing the bag from the floor where she dropped it. “I said it doesn’t make much sense. I have to go now before Dad gets mad.”

“Mary,” she turns to face Bobby again. “If you ever feel like your dad doesn’t accept you, you’re always welcome here.”

Mary smiles. “Thanks, Uncle Bobby. I’ll keep that in mind.”

When John and Mary check into their hotel room, John starts acting weird. Mary notices that he keeps drinking from his flask and twitching his eyes around. 

“So what kind of monster is it, sir?” She asks and she sets her bag down on one of the beds. 

“Pretty sure it’s a ghost, Mare.” John slurs. He throws the empty bottle in the trash and reaches for another. “Why don’t you lay down for a bit and rest up before we go research, eh?”

“Yes, sir.” She unties her boots and starts taking them off. She can hear her dad do the same on the other bed. She climbs under the covers quickly and closes her eyes. The faster she sleeps, the faster she can start hunting. 

Something hard hits the back of her head and she falls off the bed with a jolt. 

“You look just like her!” John yells. He throws another shoe at her before he rushes over to her to hold her down. 

Mary is struggling to get up but John’s hold on her is too much. She thrashes around on the bed as John sobs into her neck. 

“Daddy, get off! You’re hurting me!” 

John seems to snap out of it. He stops crying immediately and pushes Mary into the bed more. “Why can’t you be her?”

Mary whimpers, tears streaming from her eyes as John’s alcoholic breath burns them. John rears back his arm and punches Mary in the face. 

“Why can’t you be her!” He punches her again before shaking her by the shoulders.

“Daddy, stop! You’re hurting me!” Mary yells. Her head hits the headboard with a loud crack before she blacks out.

Mary wakes up and cries because of how bright it is. 

“Shut up!” John barks from the doorway. He slings a duffle bag over his shoulder. “You got injured on the hunt. I’m leaving you here to finish the job.”

Mary closes her eyes as she rubs her head gently. “But you hit me last night, that’s how I got hurt.”

John scoffs. “Now, you’re making things up, huh, Mare? I guess I shouldn’t bring you on any more hunts if you’re going to lie to me.”

“No, daddy!” Mary almost yells, wincing at the noise she made. “I won’t lie anymore, sir. I’m sorry. I guess the ghost messed with my memory, huh?”

John nods and opens the door. “I guess it did. Now, if you lie to me again, I’ll have to punish you and I don’t want to do that, okay?”

“Yes, daddy.”

“I told you to call me ‘sir.’”

“Yes, sir.”

John leaves, slamming the door behind him. Mary lets out a long sob before trying to stand. She feels nauseous so she runs to the toilet and spews bile into the toilet. She must not have eaten yesterday before the hunt.

She washes her mouth out in the sink, looking at the blood covering her face and the black eye she has. If she’s going to hunt, she needs to come up with a mantra to help her keep going after she gets hurt. She wipes blood from her nose and stares into her own eyes in the mirror. 

“Your name is Mary Winchester. You have a younger brother, Sammy, who you need to watch because daddy has to go to work. You will be the best you can be because you like to make your daddy proud. You are Mary Winchester and you need to stop lying.” 

She takes a breath in before stepping into the bathtub to wash away the evidence before they go back to Uncle Bobby’s house tomorrow. 

January 24, 1989

John drops Mary off at the store to buy groceries. She grabs a basket and looks at the list John made. She starts towards the bread section when she sees a couple of men talking to each other near the bread she needs. As she nears them, she can hear their conversation.

“...Freddie, we should just tell them. How bad can it be?” The redhead says. The brunette one sighs as he looks at the two types of bread in his hands.

“They will lose their minds, Kev. My dad will probably shoot me.”

Freddie turns to face Mary as she approaches. “Oh, hello, dear.”

Mary grips the grocery list tighter. “Hi.”

Freddie smacks Kev’s chest with his hand. “Did you, uh, need something?”

Mary points to the bread Kev’s hand. “I need to get bread for my dad. Is it alright if I take it?”

Kev smiles. “Oh, of course, dear. Where’s your dad?”

Mary shrugs. “He dropped me off here. He’s probably at the motel with my little brother. He’s five.”

The couple looks at each other, silently communicating. Freddie clears his throat. “Well, kid, it’s not safe being by yourself at the store, especially for a little girl. DO you want us to walk with you?”

Mary looks between them, the silver switchblade in her pocket is heavy next to the money John gave her. “Sure. My name’s Mary.”

Kev smiles. “I’m Kevin and this is my boy- uh, friend Alfred.”

Freddie smiles back. “Call me Freddie, Mary. Now what’s on your list?”

As the three shopped, Mary could tell that Freddie and Kevin were closer than they say. She’s seen enough of the parents at school that she can tell they love each other. As they walk out of the store with their bags, Mary asks, “So how long have you two been together?”

Kevin actually falls down when she asks it, making the contents of the bag he was holding spill all over the sidewalk. Freddie freezes in place. 

“I don’t-”

“Mary, uh-”

She smiles as she leans over and grabs a stray apple. “If it’s a secret, I won’t tell anyone. I didn’t know men could be with men.”

Kevin stands up and looks at Freddie. “Oh, well, uh, they can. Not a lot of people like it, though, so we try to keep it a secret.”

“Yeah, just like some guys turn into girls and girls turn into guys. You can do it, but not a lot of people like it when it happens.” Freddie grabs Kev’s free hand and gently rubs it. 

“Sometimes I don’t feel like a girl. Is that normal?” 

Just as Freddie was going to answer, the Impala comes to a stop in front of them. 

“Mary!” John says as he steps out of the car. Kevin and Freddie jump apart as John stalks towards them. “Get away from these fags!”

“Dad, these guys helped me-“

“Get in the car, Mary!” John yells. Kevin and Freddie step back. 

“We’re going!” Freddie says, turning Kevin around. “We’re going, sorry to bother sir.”

“Get out of here, sickos! Don’t come near my daughter ever again!” John spits at them before turning to push Mary into the car. She hits her head on the roof but John doesn’t notice. 

“Don’t ever talk to those animals, Mare.” John says on their drive back to the motel. “They’re sick. They dress up as women just to lure in kids like you to rape them. If you see any fairies again you turn and run. I’ll understand if you don’t go grocery shopping then. I’ll come in with you next time, okay?”

Mary looks out the window at Freddie and Kevin as they pass them. “Okay, daddy.”

John reaches over and hits Mary over the head. “That was an order, Mary!”

Mary reaches a hand up to where John hit her. “Yes, sir.”

November 1, 1992

She should be used to it by now. Every year on the anniversary of their mom’s death, John Winchester would take Sam to Uncle Bobby’s while he took Mary to a hotel where he would proceed to drink himself half blind and make Mary take care of him. But this time, it was different. John was quieter this time around. 

Mary brushed her hair and started to braid it back when John stepped into the bathroom of the motel. He stops in place before turning pale. Mary turns to face him, half a braid done. 

“Dad, are you okay?”

John seems to be in a trance for a few seconds before shaking his head. “I’m all good, Mare. Are you packed up? We’re heading out in a few.”

Mary ties off her braid. “Yeah, daddy, I’m all set. Do you want me to pack the car up?”

John nods his head before looking down. “Yeah, sweetie. Do that. I’ll give Sam a quick bath then we’ll go.” He almost runs from the bathroom and Mary quirks an eyebrow before grabbing her bathroom bag from the counter. 

When John checks into the motel, he only orders one bed.

“Sir, where am I going to sleep?” Mary asks. 

“With me.” John says as he locks the door, the “do not disturb” sign on the outside. “Get undressed, Mary.”

Mary looks at him with a brow high on her forehead. “What?”

John stalks towards her, eyes predatory. Mary moves to the other side of the room so the bed is between them. 

“Get undressed and lay down on the bed. If you make any kind of noise, I will hurt you. I don’t want to hurt you, Mary, so do what I say.” John pulls a gun out of the back of his pants and points it at Mary. 

“Dad-”

“Now, Mary!”

She starts to cry as she slowly undresses in front of her dad. “Please, daddy, I don’t-”

John cocks the gun. ”Now.”

Mary does as she’s told and her cold naked body sinks into the bed. John moves to unbuckle his pants with one hand. 

“Mary, from now on, you tell no one what happens on our yearly hunts, got it? Otherwise I may just kill you.” His pants hit the floor with a loud thud. Mary winces. “And I don’t want to do that. I can’t lose her, Mare, you understand?”

Mary nods slowly as she takes a shaky breath in, trying not to look at her dad’s nakedness.

“Good.” John undoes her braid before he wraps a hand around her throat and forces himself into her. She cries out from the pain and John hits her with the gun.

“Shut up, Mary! No words or you’re dead!”

Mary cries out again, trying to nod but can’t breathe. She tries to move John’s hand from her throat but he only grips harder.

She blacks out while John chants, “Mary, I miss you, you look just like her.”

Mary wakes up as she’s thrown to the floor. John sighs, and walks past her to collect his pants. Mary starts to whimper as her body comes back into feeling. Her privates burn and her legs feel like jelly.

“When I come back tomorrow,” John says as he collects his things, “I expect you to be ready to leave. We’re moving to a new town when we pick up Sam. Now clean all of this up and be ready to go tomorrow at 8.”

He starts to open the door but turns around to look at her one last time. “Oh, and if you tell anyone this happened, I’ll make sure they won’t find the body.”

Mary is sobbing when John finally leaves to go hunt whatever monster he tracked here. She slowly gets up, blood and semen dripping down her thighs as she shakily makes her way to the bathroom. She turns on the light to see her ghostly face. There is green starting to show on her neck from where John choked her. She checks her pulse to make sure she’s not dead and feels it slamming hard under the pressure of her fingers. Mary cries. Why is she still alive?

She slams her fist into the marble counter over and over again before she breathes in heavily and sinks to the floor. She grabs her hair in her hands and pulls as hard as she can.

She can’t do this. She can’t look at John the same after this. She covers her mouth to quiet the crying. 

After about a half hour on the floor of the bathroom, she feels pressure on her hands. She quickly looks up out of her hands to see no one there. The pressure is still there, like someone is holding her hands but she doesn’t see anyone there with her.

“Please.” She whispers. The pressure doesn’t leave but she feels something like lips press against her forehead. “Don’t let this be the end. Don’t let me go.”

A tear is wiped from her cheek. She feels warmth in her chest for a moment before whatever was there leaves. Mary takes a deep breath in before standing. 

Whatever monster that was doesn’t scare her because she knows John Winchester is the real monster.


	3. Cassie is the best : )

**Summary for the Chapter:**

> And homophobic and transphobic implications but it’s John Winchester what do you expect?

November 9, 1992

Mary starts at a new school on a Monday. The school year is almost over, but that’s fine with her because she already knows everything being taught. She’s so far ahead, she should be moved up a grade but she stays back for John’s sake. Mary sighs.

She called Uncle Bobby yesterday to tell him that she was going to pick up Sam from school but she couldn’t stop thinking about the last part of what he said. 

“Mary? Are you alright?” Bobby sounded worried over the phone Mary had in her hand. “Be honest with me, girl-“

“Boy,” slipped out of her mouth. She threw a hand over her mouth which made a loud slapping sound she hoped Bobby didn’t hear. There was a pause on the line. 

“Boy?” Bobby’s voice took a soft, confused tone. Mary regretted letting that slip out but she hadn’t slept the past few days taking care of John. “Mary, are you..? I mean, do you-”

“Sorry, Uncle Bobby. I was, uh, just looking out the window and saw a boy from school.” There was no way Bobby would buy that excuse. “I’m just, uh, going through, um...puberty? The hormones are going, uh, crazy right now. Sorry, Uncle Bobby, I have to go. Tell my dad that the monster you’re hunting is a wraith and can be killed with silver. Okay! Bye!”

She took a deep breath and shook her head to clear the second hand embarrassment she got from reliving that mess. She turns, looking around the motel room. The clock reads 7:46am. Mary grabs her bag next to the bathroom and quickly splashes water on her face. She stares at the face in the mirror, not recognizing the overly feminine look she dons. 

Mary reaches a hand out to trace her lips, the same lips John bit a week and a half ago. She remembers him telling her that she was such a pretty girl, so lovely, Mary-

She can’t go by Mary anymore. She can’t hear that name without thinking about...that. She doesn’t even feel like being Mary, let alone being a girl right now. She remembers how that gay couple told her that it’s okay to be gay but what about being a different gender? She doesn’t feel like a girl, especially after that night. What about...is a name change too much? 

She stares into her own green eyes in the mirror before whispering a new mantra, “Your name is...your name is Deanna Winchester. You have a younger brother, Sam, who you take care of because your dad isa hunter. Your mom died at the hands of a demon which is why you have to take care of Sammy. You want your dad to be-“ 

She slams a fist on the counter. She can’t say it. She looks at the clock again. 7:52. She can’t say it. 

Mary- no. Deanna. No, that doesn’t sound right either. She scrubs a hand down her face and sighs. Dee. Dee works.

Dee brushes her hair back and walks out the door. She arrives at school by 8am. 

December 14, 1992

Dee’s is the only kid in her class whose parents aren't here. Her dad could not get the day off work, or so she told her teacher. In reality, John has been gone almost two weeks working a few cases with some brother duo named Saul and Dan. While he’s gone, Dee has been taking care of Sam with the money John left for them. It’s just about out now. She’s resorted to taking the school lunch home to feed Sammy and eating whatever he doesn’t finish. 

The door to the classroom opens as she debates whether or not to call Uncle Bobby to help them. The woman who walks in introduces herself as Jane’s mother. Jane Trinnison was a bitch who always shoved Diana around because she thought Dee was too much of a tomboy. 

“Class, let’s pay attention to what Miss Trinnison has to say.” Mr. Willer says, tapping on the chalkboard. Dee looks up. Miss Trinnison has a square jaw and seems to be hiding something. As she talks, Dee tries to figure out what she could be hiding. An affair? No, because she wasn’t married. She must have divorced her husband because of something. Is she hiding abuse like Dee does? She looks for bruises while Miss Trinnison goes on about being a counselor or something for a school. Boring. 

When she finishes talking, Mr. Willer asks if anyone has questions. A few hands shot up, but Kelly Trinnison is focused on the little girl with long blonde hair who’s staring at her. She can see hurt in her eyes and wants to know if she’s okay. She answers the kids questions and waits outside when she’s done. Jane’s other mom was picking her up today so when class was dismissed, Kelly told Jane that Sarah was in the parking lot waiting for her. 

“But I don’t like Frank, mom.” Jane said, shifting the bag on her shoulder. “Can’t I go home with you?”

“Jane, your mother wants to take you this week because her and Kevin will be gone this weekend.” She reaches out to tuck a hair behind Jane’s ear. “We’ll do something fun this weekend, okay?”

Jane sighs and looks away, “Why couldn’t you stay my dad so I didn’t have to see Kevin?”

Kelly looks down. “Janie Bear, I couldn’t live a lie. I wish sometimes I didn’t have to be like this just to see you more but I…” Kelly squats down and takes Jane’s hands in hers. “Listen, kiddo, I love you, okay? Go to your mom and try to have fun. Just remember we'll have the weekend and all of next week together, alright? I need to talk to your teacher now but I love you.” Kelly stands up and kisses Jane’s head. 

“Okay, mom. I love you, too.” Jane runs off with the rest of the students and Kelly looks for that blonde girl. 

She can see her in the classroom still, Mr. Willer talks to her about something. She walks in the classroom again. 

“...missing the last three homeworks still, Miss Winchester. I need you to turn them in by the end of the week and I won’t mark down any points for it being late. I’m concerned for your grade, that’s all.” 

The girl finally looks up to meet Mr. Willer’s eyes. “Okay, sir. I’m sorry.”

He sighs before turning to look at the door. Kelly waves at him. “Sorry, Mr. Willer. I just wanted to talk to Miss Winchester before she left.”

Mr. Willer walks over to his desk. “Of course, Kelly. Mary, I know you’re new here but I can’t take that as an excuse anymore. I’ll be back in a few, I need to go to the teachers lounge for a meeting.” 

Kelly walks up to the desk next to the girl’s and takes a seat. “Are you doing okay, sweetie?”

Dee looks at her hands. “I’m fine, Miss Trinnison. What did you want to talk about?”

“I notice you kept staring at me earlier. Was there anything that I did to bother you? I’m sorry if there was.”

“No, you’re fine, ma’am.” Dee looks up at her. “I was just wondering what you were hiding. But you don’t have to say it if you don’t want to.” She quickly adds on. 

Kelly was taken aback. How did a twelve year old girl recognize Kelly was hiding something. She realized she hadn’t responded for a few minutes. 

“Sorry, that caught me off guard. Um, why do you think I’m hiding something, Mary?”

“I go by Deanna, not Mary.” 

“Oh, I’m sorry, Deanna. Can you tell me why you think I’m hiding something?”

Dee smiles. “You mean after that convincing argument?” She shifts in her seat, reaching towards her bag. “You hold yourself differently. That’s all. I won’t tell Jane if you’re hiding something from her, I know Christmas is coming up and you must have found something really great for her.”

“No, that’s not…” Kelly sighs. “I’m not hiding anything from Jane. I was hiding something from the class. Not a lot of people know this but...Dear, what do you think of people who are gay?”

Dee was caught off guard. She pauses for half a second before continuing packing up her things. “My dad says they’re sick and they need to get better. He also told me about how gays dress up as women to trick normal guys into dating them or that the men will try to get close to kids while dressed up so they can rape them.”

Kelly freezes at hearing a twelve-year-old girl say the word ‘rape,’ and swallows. “But what do you think?”

Dee doesn’t answer. She can’t answer. If she tells this lady that she might be gay- or worse that she feels like a boy more than a girl - her dad will figure it out. “I...I don’t-“

Kelly smiles softly. “You don’t have to know right now. But I’ll let you in on a secret: Gay people aren’t sick. They can’t help the way they feel. And if your daddy says something about the bible saying it’s wrong, God never said that. In fact, God said that a man shouldn’t have any sexual relations with children. The translation is off from the original hebrew. As for men who “dress” as women, those people are called transgenders. And, well, just like people can be gay, there are people out there who are transgender. I used to be a man.”

Dee almost cracks her neck with how fast she looks up. “That doesn’t sound...right. You can do that? Just change gender like that?”

Kelly smiles softly. “Yes, you can. Not very many people change genders. There are people out there who will kill you because of it and claim God thinks of us as monsters. That’s actually false. If God made us in His image, then why can’t we switch between genders? They're both God’s image so who cares?” 

Dee is still in shock, her eyes are glazed over and she doesn’t pay attention to anything Kelly says. “You can...like if I wanted to be a boy I could?”

Kelly smiles. “Do you feel more like a boy?”

“I…” Dee wrongs her hands together. “I never- My dad calls me a girl and it makes me...zone out sometimes. Like it’s wrong.”

Kelly nods her head. “It feels like it’s not right but you can’t really explain why.”

“Exactly!” Dee takes a deep breath in. “And even though I can do things better than my dad, sometimes, he never listens to me because he calls me a girl but I don’t feel like a girl. So, maybe, I’m a boy.”

Dee stops breathing. Maybe that’s what has been wrong this whole time. Maybe if she became a boy, her dad would listen to her and appreciate her. 

“Well, son,” Kelly pats Dee on the shoulder. “I’m proud of you, whether you’re a girl or boy. Any adult would be lucky to have you.”

Mr. Willer walks into the classroom. “Everything okay, ladies?”

Dee stands up. “Yes, sir, I was just packing up my things. I’ll have everything for you tomorrow. I’m sorry, again.”

He smiles. “No problem, Miss Winchester. By Friday is okay, too.” Dee runs out of the room, already late to pick up Sam. “Miss Trinnison, I hope everything went alright?”

“Yes,it went well, Jared.” She smiles and starts towards the door. “Deanna just had a few questions about being a school counselor, like me. I hope I gave her enough motivation to do well in school.”

“That’s exactly what she lacks.” Jared starts to gather papers from the desk. “She’s a great student, extremely intelligent. She just doesn’t turn in work to show it. I may have to call home to see what’s going on, but as long as she turns in the late work she should be fine.”

“I do wish her the best.” Kelly checks her watch to see that it’s 3:30. “Well, Mr. Willer, I must be on my way. I’m running late for a meeting of my own.”

“Take care, Kelly! And tell Jane that her project was very well written.”

April 21, 1997

Dee sits in the principal’s office, leather jacket creaking as she crosses her arms. 

“You want to drop out?” The principal asks. “You only have a little under a month left, are you sure?”

Dee nods. “I need to change my work hours so I can take care of my brother. My dad is picking up more hours and I need to do the same. Sam wants to go to college and we have to save up.”

Principal McDonald nodded. “I understand, but don’t you want to go to college as well? You’re the best student in your grade, you have a bright future ahead of you, Deanna.”

Dee shakes her head. “If you think I’m the best, you should see my brother. He’s going to be famous one day.”

Dee shifts her weight in the chair. “Look, Principal McDonald, I know There’s a month left. I would continue if I could, but I really need to start working, especially now. My dad was injured on the job last week so we have no income right now. I have to pick up more hours or another job to help him.”

Principal McDonald sighs and leans back in his chair. There’s a few minutes where neither of them talk. 

“What if,” the principal says, leaning forward in his chair. “What if I get your teachers to let you take the finals early? We can rush your diploma and you’d graduate early.”

Dee perks up. “You can do that?”

“We can. You just have to give us until Friday.” Principal McDonald flips his calendar open. “You can take tomorrow and Wednesday off and come back on Thursday and Friday to take the tests and get your diploma.”

Dee let’s put the breath she didn’t know she was holding. “Thank you, sir. I can do that.”

“Great! I’ll get everything ready and make sure you’re all set for Thursday.” He stands up from his chair, signaling to Dee to stand as well. They shake hands as he continues, “Don’t worry, Dee, I understand you have to do what your family needs.”

Dee nods and gathers her bag. “Thank you, again, sir, for this opportunity.”

As she leaves, he says, “Take care.” 

She smiles. “Thanks, same to you.”

She ends up getting her degree but she tells Sam that she dropped out. 

May 24, 1997

Dee and Cassie are laying on the picnic blanket staring at the clouds. It’s probably the only day Dee has had off in almost three weeks and she wants to spend it with someone who cares about her.

“Cassie?” Dee asks. 

She looks over at Dee. “Yeah, Dee?”

“Would you hate me if I told you I think I’m a man?”

Cassie sits up right away. “What makes you say that?”

Dee sits up to face her. “I just...I’ve always felt wrong being a girl. It’s the only thing that makes sense.”

Cassie nods. “Okay. Well. Would you hate me if I said I’m attracted to you?”

Dee starts. “What makes you say that?”

“Well,” Cassie takes Dee’s hand. “If you feel more like a boy, then me suggesting we date instead of just being friends would be alright. I wouldn’t have to have this crisis of whether or not I’m gay because you’re a boy not a girl.”

Dee stares at Cassie in shock. 

“What?” She asks. 

Dee leans in closer to her. “So if I asked you to call me Dean, you wouldn’t mind if I kissed you right now?”

Cassie smiles as she closes the distance between them. “I would say hurry up and kiss me, Dean.”

Dean slides his mouth against hers and feels whole. He could burst into tears at this moment. 

Dean ends up sleeping over at Cassie’s house that night, earning him a beating from John but he couldn’t be happier.


	4. Quick! Kill me so I don’t have to deal with my problems!

**Summary for the Chapter:**

> no proofreading at all. we die like men. 
> 
> Crowley is a low level demon and kills his competitors to become King of Hell, change my mind. (I don’t remember anything about any season before 14, 15x20 destroyed those memories for me)

December 25, 1997

Dean takes a few pictures of Sam as he opens up his presents. John had already opened his gift of a new knife and gun set from both Sam and Dean along with some whiskey from Bobby. Bobby is pouring everyone some eggnog while they sit in front of the fire. 

“No way!” Sam yells as he pulls out a couple of books from the wrapping paper he shredded. Dean smiles widely as she looks at Sam’s face. “You got me pre-law books, Mary? How did you know?”

John glares at Dean while she collects the wrapping paper. “You’ve talked about it nonstop the entire summer, how could I not?”

“You’re the best, Mare.”

“Sam,” John says roughly. “Why don’t you open your last gift from me?”

Dean looks at John quickly. Sam already opened a gift from John- a leather jacket Dean had picked out this past November before she wasn’t able to go out in public because of the two black eyes. 

Same shuffles over and grabs the last bag from under the tree. “I thought this was Mary’s.”

“Mary already opened her gifts while we were waiting for you, Sammy.”

Dean swallows. She hasn’t gotten gifts for Christmas since she was six but she’s not going to tell that to Sam. She tries her best to make sure Sam always has the best gifts and if that she doesn’t get any, then so be it. Besides, she’s going to Cassie’s house tonight so she’ll be able to get something then. 

“Dad?” Sam’s voice is soft. Dean looks quickly to Sam’s hands and sees a shiny pistol sitting in them. “What is this?”

John stands from the sofa. “Your very own gun. Now that you’re old enough, I’ll start taking you on hunts so you can learn how to handle yourself out there.”

Sam shakes his head slowly. “Dad, I don’t want to hunt.”

Dean holds her breath as she pauses in her collection of the tissue paper. John’s jaw twinges under the force of his anger. 

“What did you just say?”

Sam tilts his chin up. “I said I don’t want to be a hunter. I want to be a lawyer.”

“You’re a Winchester.” John stands and slowly walks to Sam. “Winchesters are hunters, not some kind of a pansy assed guy in a suit. You’re coming with me on the next few hunts I have, low-level stuff to ease your way into it.”

Sam’s face shows a mix of disbelief, anger, and shock. “You can’t make me!”

John throws his hands out and looks around the room. Dean knows she’s made a mistake after she says, “Sam,” in a soft voice and the two other Winchesters glare at her. 

“Stay out of this, Mary.” John almost growls at her. Dean shoots Sam a look she hopes says “please humor him or else I’ll get your punishment” before she leaves the room. 

Bobby is finishing pouring the drinks when Dean walks in. 

“Need any help?”

Bobby jumps. “Jesus!”

Dean smiles. “You know, for a hunter you’re very jumpy.” She grabs a couple of the drinks and moves them to the table. “We might want to wait here for a few more minutes.”

“Why’s that?” Bobby asks as he sits next to her.

“Dad gave Sammy a gun and told him that he’s going to be a hunter.” Dean sniffs a couple of the eggnogs, looking for one that’s spiked. 

Bobby scoffs. “That kid has been dreaming of being a lawyer since he saw ‘A Few Good Men.’”

Dean rolls her eyes. “I know that. I was the one who bought him his first suit and all those lawyer books.” She takes a sip of the eggnog before continuing. “They’re both stubborn as mules. Once they have an idea planned, they’ll do anything to finish it. Only thing we can do is make sure they don’t come to blows.”

“I’ll drink to that.” Bobby lifts his drink to Dean’s before taking a gulp. “Guess I should break it up before I have to buy any new furniture.” 

Bobby reaches into a cabinet, pulling out a card. “Before I forget, I gotchu something. It ain’t much, but I figure you and Cassie can go to a nice place and get some rich guy’s attention.”

Dean quirks his brow before opening the card to see a check for five-hundred dollars in there. 

“Uncle Bobby, I can’t possibly take thi-“

“Mary, you take that and use it for yourself. Not for your dad or for Sam- for you. I know you haven’t gotten a lot of gifts, especially from your dad, but I want you to take this. God knows you might need it if your dad doesn’t come back from a hunt.”

Dean has tears in her eyes. “Thanks, Uncle Bobby.”

Bobby nods before walking toward the ever-growing noise from the living room. Dean folds the check and puts it in her bra. She’ll deposit most of it to Sam’s college fund she started and keep about a hundred just in case. 

She takes her mug and makes her way upstairs to her and Sam’s room. She sets the card on the nightstand, slipping a twenty in place of the check in case John or Sam come in and see it. She grabs her overnight bag and packs up her things, keeping the check in her bra in case John flips out and goes through her things. Dean grabs the box she stashed in Sam’s things and sets it in the bottom of her bag. Cassie is going to love it. 

Dean zips it up and sets it by the door. As she is leaving the room, she can hear Sam sniffling and finds him sitting on the bottom of the stairs. 

“John, I don’t know why you’re forcing him to do something he clearly doesn’t want to do.”

“You’re not his father, Bobby,” John is right next to Bobby pointing a finger in his face. “I am.”

Bobby scoffs. “You’re in my house and as long as that is, you’ll abide by my rules. Sam goes on hunts when he wants to, he’s still in school, anyway. He can’t miss too many days.”

John twists his face into a glare for a second before he looks down and steps back. “Fine. For now.”

John spots Dean by the stairs by Sam. “Mary, pack your bag, we’re leaving.”

“What?” Sam says, standing quickly. “Where are you going?”

Dean nods. “Yes, sir.” 

She starts to go back up the stairs but turns backs while Sam starts up another argument with John. “Uh, Uncle Bobby? I need your help getting my bag, it’s, uh, too high for me to reach.”

Bobby looks at her quizzically. Dean shrugs her shoulders and mouths, “Cassie’s present.” 

“Oh! Yeah, sure, Mary.” Bobby nods and heads up stairs with Dean. 

She opens the door quickly and rips open her already packed bag. She hands Bobby a small wrapped box. 

“Can you drop this off at Cassie’s and tell her I can’t make it? Please?” The words rush out and she holds her breath. 

Bobby takes the small box and nods. “Sure thing, kid. How about you write me a note saying where she lives and what to say.”

Dean nods and rushes around the room to find a piece of paper. When she finds it and starts writing, Sam rushes into the room. 

“I’m sorry, Mary, dad says you have to go. He was going to take me but I’m supposed to hang out with Derrick and Tony tomorrow. I tried telling him he could hunt alone but he wouldn’t listen.” Sam sits on his bed and puts his head in his hands. “God, why is he so pissed off!”

Dean looks at Bobby. “Dad’s been through some shit, Sammy. He doesn’t know how to express his emotions.”

Dean folds the paper and then writes Cassie’s address on the front. “Here, Bobby. Oh, can you also deposit this? It’s my last paycheck.” She hands Bobby the check he gave her. “I wrote down the numbers next to the address. Thanks again.” 

“Address?” Sam perks up. “Do you have a boyfriend or something?”

Bobby leaves the room as Dean hits Sam with a pillow. “No, bitch, it’s for my friend Cassie. I was supposed to visit her today but it’s okay, I’ll visit when I come back.”

“Mary,” Sam starts. “I know you like it, but maybe you should tell dad you don’t want to hunt.”

Dean jerks back. “What?”

“It’s not because you’re a girl!” Sam stands up and puts his hands on her shoulders. “It’s just...you get so banged up after every hunt you go in with him. it’s like he uses you as bait or something.”

Dean looks down, furrowed brow drawing lower on her face as she makes a knee-jerk decision. “Yeah, well, better than him doing it to you.”

Sam jumps away from Dean. “You mean you’re his bait?”

Dean shakes her head. “No! He doesn’t use me as bait. Jesus Christ, Sam, I just meant that you hate hunting. I actually enjoy it. So what’s the big deal if I get a little scratched? I’m fine so it’s fine!”

Sam frowns. 

“Plus with a face like that, you really don’t need anything else to mess it up.”

Sam squeaks out a ‘hey!’ and then pulls Dean into a headlock. 

“Mary!” John yells from downstairs. “Let’s go!”

Dean pushes away from Sam and grabs her bag. “Take care, Sammy. Study hard! Harvard ain’t taking any B’s, bitch!”

“I want to go to Stanford, Mary.” Sam sits back on the bed.

“Same tea, different kingdom.” Dean closes the door and heads downstairs. 

When they make it to the motel, Dean can’t walk because of a broken ankle, courtesy of John Winchester after he lost the werewolf. 

January 24, 2000

Dean was sipping on a beer while he sat in a lawn chair at Bobby’s house. Sam was with John on a small time hunt. John has been taking Sam on more and more hunts, each time ending with an argument from Sam that usually went like this:

“Dad, I don’t want to be a hunter! I want to go to college! Have a normal life!” Sam would say.

“You would let your mother’s memory die just like her, huh?” John would reply, making Sam feel guilty about ever arguing.

After all this, John would hit Dean for as long as the argument took. The longest time was two hours. Dean had a hard time explaining that one to Bobby the next day.

“Mary? You okay?”

Speak of the devil. “Hey, Uncle Bobby.” Dean looks up at him and smiles. “Didn’t know if you were here or not; thought Sam must’ve finally put you in a home.”

Bobby pulls up a chair next to him. “You know, I’m old but I ain’t senile yet.”

Dean smiles. “Do you know when Sam will be back?”

Bobby sighs and takes a long sip of his beer. “John says they’ll be a couple of days. I already called the school for Sam.”

“Good. That’s good.” Dean looks down at his watch. “I’m going to hang out with Cassie tonight. I’ll probably sleep over at her place.”

“That’s fine with me, Mary. You’re not 16 anymore, you don’t have to ask me for permission or anything anymore.”

Dean nods and they sit in comfortable silence for a bit.

Bobby can tell something is wrong. He continues to sit and wait for Dean to tell him what’s bothering him as the sun goes down. 

Dean runs through his plan again before he shakily says, “Uncle Bobby?”

“Yeah, Mary?” Bobby sets his beer down. This is probably going to be a deep conversation if Dean sounds shaken up. “What’s wrong?”

Dean’s face scrunches and tears start to fall. “If I told you I was actually a man, what would you say?”

Bobby leans back in his chair. He goes through his memories of Mary and recalls moments where she would seem to be more of a tomboy than a girly girl. The long arguments for school dances where she didn’t want to wear dresses, the flinches whenever Bobby referred to her as ‘she’ and Mary a few years back. He knows this didn’t come out of nowhere, but he still feels surprised. 

“I would ask you what you meant by it, kid.” 

Dean lets out a breath. “Well, uh, Uncle Bobby- I think I might’ve been born in the wrong body.”

Bobby nods. He turns to look at the sunset. “Why do you think that?”

Dean has tears falling down his face. The presence he once felt back when he was first raped returns. A warm pressure holds his hand and he feels a renewed sense of purpose. “I...I don’t think I ever really felt like a girl. Before mom died, I remember being made that I wasn’t a boy and therefore couldn’t take a bath with dad. Ever since then, I never felt like I was a girl but I just…” he sighs. “I just ignored it. And then dad-“ Dean grips the bottle hard. 

Bobby notices. “What did your dad do?”

The presence is still there. Still comforting. 

“He...he hurt me.”

Bobby nods. “I’ve been noticing that he hits you. I don’t know how to help you-“

“No.” Dean says. “It’s not that. I deserved that.”

“Mary, no one deserves that.” Bobby says, placing a hand on Dean’s shoulder. “No kid should be hit by their own parent.”

“No kid should be raped year after year either but that doesn’t stop John from doing it.” Dean whispers. The presence moves to the back of his neck. 

Bobby is shocked. He doesn’t speak for a while. Dean sits there worried the entire time. 

“How should I kill him?” Bobby asks, voice rough and low. 

“You don’t,” Dean says. “I’ll do that when the time comes. For now, I find a way to leave so I can live my life as the man I was meant to be.”

Bobby nods his head. He’ll beat John to a pulp on the next hunt and blame whatever monster they hunt. “So if you’re a man, have I been calling you the wrong name this whole time?”

Dean is shocked. He didn’t expect that question nor did he expect Bobby to not blink an eye at him killing his own dad. 

“Well, son? What should I call you?” Bobby takes a sip of his beer. “I may not fully understand, but I’ll try to make you as comfortable as I can. It’s the least I can do as your friend.”

Dean stands up and tackles Bobby in a hug. Bobby drops his beer to catch her- him. To catch him in his arms before Dean breaks down in tears. “Bobby, you know you’re more of a father to me than John ever was. Fuck outta here with the friends crap.”

They sit there, each of them crying for a while. The sun is fully down by the time Dean stands back up. 

“I want to go by Dean. Dean Robert Winchester.”

Bobby smiles at hearing his name being one Dean chose for himself. “Not Singer? Didn’t think you’d want your dad’s name after what he’s done.”

Dean smirks. “Well, as the Winchester who wrote the famous Winchester Hunter Journal, I feel like I should keep the name.”

Bobby gaps at him. “You wrote it? I thought John did.”

Dean shakes his head. “Everything John said he knew was actually because I told him. I wanted to be a hunter back when I was six years old. I researched everything I could and even built that Walkman EMF detector he said he built.”

Bobby is speechless. “You built that? When?”

Dean shrugs. “When I was probably eight. It was pretty easy, I was reading up on how to fix cars and appliances at the time and tried my hand at building it. Anyone could do that.”

Bobby shakes his head. “No, not anyone.” 

Bobby stands up and pays Dean on the shoulder. “You’re special, kid. I always knew that.”

Dean gives him a small smile. “Thanks, Bobby.”

Bobby nods and starts to head inside. He stops and turns to Dean one last time. “So, does Cassie know? Or…”

Dean laughs. “Of course she knows. I know I told you we’ve been friends since I was seventeen, but we started dating when I was eighteen. Cassie knows everything, Uncle Bobby. I think she might be the one for me.”

Bobby smiles. “In that case, I don’t know if you should sleep at your girlfriend's house until you give her a ring.”

Dean’s jaw drops. “Bobby!”

Bobby laughs as he makes his way into the house to order some takeout for himself. 

November 2, 2000

Dean looks over at her dad who was pouring himself a shot in the dim motel room. 

“Now, Mary, I’m hunting an actual demon today with Jeff Stran, so I need you to make sure my bag is packed with things that will help me with a demon. You have that written in the journal, right?”

Dean nods. “Yes, sir.” 

Dean made a journal with all the information on monsters they’ve- John- encountered and how to kill them. John took the credit for it all, but he wouldn’t be able to kill anything if it wasn’t for her. She’ll make sure that John can’t hunt after she leaves. 

When she leaves, she’s taking the Journal with her.

“Sir?” Dean stands up and looks at John’s face for a second before looking down at his boots. “Is it alright if you leave the journal here so I can add more information about Wraiths I found?”

John swishes the shot of tequila around his mouth, debating whether or not to let her keep it. 

Dean shifts from one foot to another. “I can also search more on other creatures and add to that for you so after this hunt, you don’t have to research about wraiths much. I was looking through the paper and saw something that could be a wraith not far from here.”

John nods and swallows the liquid. “That should be fine, Mary, but I want you ready for me when I get back. I’m going to the bathroom, I expect the car to be packed with everything by the time I get out.” He slams the glass down and heads to the bathroom. 

Dean sprints around the room collecting everything John would need before rushing out of the room to put the heavy bag in the car. While she’s closing the Impala door, a truck pulls up next to her. 

“Hey, Doll, do you know if John Winchester is here?” The man in the truck asks. 

“Jeff!” John yells from the room. “I’ll be right down.”

Jeff exits his car and looks Dean up and down. “So, what’s your name? Are you a hunter, too?”

“Leave my girl alone, Jeff.” John opens the impala door. “If she doesn’t kill you then I will. Are you ready to go?”

“Sure am.” Jeff says. He pats the impala’s roof. “You sure you want to take two cars? I’m sure if we both go in mine we’ll be alright.”

John stiffens. “What are you suggesting, Jeff? That you think I’ll ditch you?”

“No! Nothing like that, I swear.” Jeff’s looks at Dean. “It’s just more fuel efficient. I just filled up mine on the way and I’m sure you haven’t refilled from the drive down here yet. I was just trying to be helpful.”

John squints. He looks at Dean before nodding. “Alright, that’s fine. Mary, be sure to fill her up for me so we can leave early tomorrow for that wraith case.”

Dean jerks her head in a quick nod as she catches the keys John throws her. 

“Don’t forget to update the journal with the notes I left you. We’ll need it tomorrow.” John grabs the bag and walks to the passenger door of Jeff’s truck. “Let’s get going, you can debrief me on the way.”

The two men leave and when Dean can’t see the tail lights anymore, she gives a quick fist pump. 

“Yes!” 

She runs back inside and quickly packs everything she has. She’s finally leaving. She has the journal and the car, she’ll be fine. She slings the bag over her shoulder and turns to see a man leaning on the door of the room. 

“Hello, darling. I’ve been waiting for you.” He says with a twang of an accent. 

Dean looks around the room for a weapon but remembers that John took them all. She looks back at the man. “What do you want?”

The demon smiles as his eyes shift to black. “Well, Mary Deanna, you’re daddy has been killing a lot of my- ow!”

Dean threw her duffle bag at him while he was talking. It hit him in the face with a smack, the extra boots doing a number on his nose. She takes her silver switch from her pocket and stabs him in the chest. 

The demon glanced down at where Dean had stabbed him. “Oh, darling,” he pulls out the blade and drops it on the floor. “I’m afraid that doesn’t do anything to me.”

Dean shoves the demon and books it out the door, grabbing the keys from her pocket as she runs. She feels a hand on the back of her jacket before she’s pulled down the Hall back into the room. 

“Stop it!” The demon yells at her when she lands on the floor. “I’m trying to help you, you idiot!”

Mary sits up, rubbing the back of her neck. “What do you mean you’re trying to help me? Aren’t you just looking for a deal?”

The demon shrugs. “Well, yeah, but I’ve been keeping my eyes on you Winchesters to see if the golden ticket was true or not. Turns out, John’s success wasn’t because of himself but because of you.” He steps closer to Dean. “So tell me, why does an intelligent girl like you stay with a drunken lowlife like your dad?”

Dean looks around the room, judging her options. She can exorcise the demon but she will need time to do so. She doesn’t have any type of demon-killing weapon or holy water so she may have no other choice. “Why do you care, demon?”

“Now, Mary, don’t be so mean to me, I thought we had a connection. Please, call me Crowley.”

Dean quirks a brow. “Alright then, Crowley, why do you care?”

Crowley squats down so he’s at eye level with Dean. “Because I know he does more than beat you.”

Dean scoffs. “Is that supposed to scare me? So a dad beats his son a little, no harm no foul. Dad rapes me once and there’s no one. No one to intercede: no angels, no demons, no nothing. Second time I expect something to change. For someone to see how wrong it is. I tried fighting it one year and he threatened to beat my brother. I don’t have a fucking choice.”

Crowley pushes his tongue around his mouth, feeling somewhat ashamed but mostly feeling angry at himself for feeling so. 

“So if you’re trying to make a deal for me to not have to deal with John anymore, suck balls, man. I won’t let Sam take the fall of what will happen.”

Crowley nods. “What if I can guarantee Sam will be safe? How old is he, anyway? Does he know about the abuse?”

Dean rubs a hand down her face. “He’s seventeen now. And no, he doesn’t know. He doesn’t know a lot of things.”

“Well, let’s keep it that way. And I’ll do this pro Bono, darling. I’ve taken a liking to you, Winchester. You’re so full of rage it’s Devine.” Crowley stands up and looks around the room. “What do you say we fake your death by my hands and I pop you somewhere far away from here for a bit while I clean up loose ends?”

“I’d say you’re absolutely crazy, Crowley. How can I trust that you won’t release your hounds on me later?” Dean stands up, looking down at Crowley. 

“Like I said, Dean, I like you. I know your head.”

Dean jumps at the use of his chosen name. “How do you know that?”

Crowley tuts. “Mind reading is a higher demon's power. You know, I’m sure your dad wouldn’t mind if you told him you’re trans.”

Dean scoffs. “Yeah, maybe if I wasn’t an exact copy of my mom it would have been fine. I look too much like her so if I change anything about my appearance without his permission I get a beating and a hell of a lot worse than if I sit there and look pretty for him.”

“This,” Crowley says while pulling a lighter out of his pocket. “Is why I’m getting you out. Who knows, Dean, maybe we can share a night together sometime.”

Crowley lights the bed on fire. It slowly spreads across the sheet. 

“So what the hell do I do for now?” Dean grabs the Journal and his blade from the floor. 

“I’ll ask for two things in return for getting your new life set up.”

Dean looks over his shoulder at Crowley. “I thought you said this was pro-Bono.”

“Technicalities.” Crowley waves his hand. “I want you to keep that journal out of John’s hands.”

“Done.” Dean tucks the Journal into his pocket, making sure all of his things stay in the room. “What else?”

“I’m trying to become the king of hell. If you just happen to run into any demons on this list-“ he pulls out a sheet of paper. “-then I need you to kill them.”

“Kill them how?” Dean grabs the paper from him and reads through the few names on the list. “I can pretty much send them back to hell, anything else I haven’t figured out yet.”

“Lucky for you, Dean-o, I have an extra demon blade.” Crowley hands Dean a long silver-looking blade. “But you didn’t get any of this from me.”

Dean nods and walks out of the room, Crowley on his heels. “So where are you stashing me? I assume you’ll get a body double- an already dead-“ Dean gives Crowley a pointed look. “Body Double for the room?”

“Yes, already done.” He snaps. “You’ll take the car to a hide out in Rochester and when I’m done, I’ll meet you there to give you directions to your new safe-house.” 

“You know, Crowley, this sounds too good to be true. How do I know you’ll keep Sam safe?”

Crowley holds his hand out so Dean can take the keys to the Impala. “Because, if John loses you, he’ll never stop hunting for me leaving Sam to be in the care one Robert Singer. It would only be for a few months before he’s off to college- and no, I can’t help him get into college.”

Dean frowns but nods. “Figures.” 

“Right, well, Sam’s little trust fund will have a few more pounds to it, but I’ll make sure Sam gets any last will and testament you have stored somewhere.” 

Dean nods, planning to write everything down on notebook paper. “Can I give you something I wrote and you copy it someplace more official?”

“I can do that.” Crowley looks down at his watch. “Now get out of here the cops should be on their way soon. Ta!” 

Crowley turns and heads to a small red car at the end of the lot. Dean opens the driver door and gets in. He starts the engine and drives, not looking back to see the fire engines arrive. 

John and Jeff were sitting in the truck, watching for any signs of movement in the shed. 

“I don’t see anything, John.” Jeff sighs. “Maybe we go in and check the joint.”

John nods. “Sounds good. The demon has to be here, it's his hideout.”

They get out of the car and make their way towards the door. As soon as they open it, a voice says, “Hello, boys.”

John recovers from the shock first, turning with his gun held steady. “Who the hell are you?”

“Who’s asking?” Crowley sticks his hands in his pockets. 

John holds his gun firmer. “John Winchester. Now answer.”

“The famous John Winchester.” Crowley smirks. “I just visited a Mary Winchester, any relation?”

John’s blood goes cold. “What?” 

Jeff finally gets over his shock at this point. He starts to chant the exorcism but Crowley sighs and snaps his finger. Jeff explodes in place, prompting John to cover his face. 

“Funny,” Crowley says, brushing some blood from his suit. “Mary did say she didn’t care for him. Too... what’s the word. Desperate.”

John shoots him. Crowley grabs his shoulder to feel the blood gush from it. “This was a new suit!”

“What did you do to Mary!” John yells, spit flying out of his mouth. 

Crowley smirks. “Just had a little fun with her. A little bit of torture, a little bit of nasty; you would know. She said she would have preferred you over me with everything I got to do before she ended up like her namesake.”

“What did you do!” John shoots again but Crowley moves out the way. 

“Why don’t you check your room?” Crowley smirks and walks out the door as John flails for his holy water. 

Crowley walks away and imitates the sound of the Impala starting up before he hides. John runs out of the shed and screams before going back in the shed. He emerges after a few minutes and starts up Jeff’s truck before speeding away. Crowley laughs softly. He’ll be king of hell soon and he can’t wait for John to arrive there. He has some plans for him already. 

November 6, 2000

He pulls through a McDonald’s and orders a few hamburgers and a coffee while in Albany. He has to find a job and then hopefully a cheap place to crash. 

After checking into a shady motel, Dean grabs his switchblade and looks in the mirror. He sets the blade on the counter and then starts sectioning off his hair. He knows he’ll have to get actual clippers, but if he gets it as close as possible now he can worry about that later. 

He starts with the back section and holds the sharp edge to his hair. This is it. After this, he’ll officially become a man. Dean Robert Winchester. Dean. 

He sets his blade down and punches the counter, talking a shaky breath in. 

He can’t do it. John will find him and then probably kill him if he does it. 

“John’s not here.” he whispers to himself. He picks up the knife again. “Just do it, pussy.”

He cuts through the hair easily. He holds the braided piece in his hand. Almost a foot of hair just gone. Just like that. Dean starts to laugh. 

He cuts off all the sections before stuffing the hair into a garbage liner. He could probably donate it to some cancer clinic for a wig or two. 

Dean looks in the mirror and starts to cry. His hair is choppy and is closer to a zombified mullet more than an actual close shave, but it doesn’t matter. Mary Deanna Winchester is dead. 

He’s finally Dean.


	5. What’s Up, Bitches?

**Summary for the Chapter:**

> short chapter but that’s because the next one is emotional. 
> 
> I’m writing it as you read this so you know it will be a ride. I should have it done either tomorrow or the next day. After ch 6 I’ll bring in Cas. Maybe more than 10 chapters what was I thinking? let’s pretend I said 15 and that I’ll finish before January ends? I have a lot ideas I wrote down and then decided to lengthen almost all of them. everything written was supposed to be like one or two chapters lmao

November 7, 2000

Sam doesn’t know how to react. Bobby is devastated at the funeral. John stares at the ground where they bury an empty coffin like it pissed in his coffee. 

It’s a short service, just the three of them and Mary’s friend named Cassie. Cassie cried the entire time, talking about how she would miss her best friend. Her and Bobby talked after the service while Sam and John got into the Ford Mary and him fixed up the year prior. 

“We’re going on a hunt. A small one.” John’s voice demanded no response so Sam just nodded. He didn’t want to think about how Mary died on a hunt that John said was going to be a small one. 

“Did you know?” Bobby asked Cassie as the Winchesters drove off. 

“Know what?” She asks, tissue coming up to wipe her tears. 

“Know about...Dean Winchester.”

Cassie nods and leans on Bobby’s truck. “I was his girlfriend, of course I knew. When did he tell you?”

Bobby smiles. “At his twentieth birthday. He told me a little about you but I wanna know how you two met.”

“Of course he waited until after he gave me a promise ring to tell you.” Cassie sniffles and plays with the silver band on her wrist. 

Bobby’s eyebrows climb to his hairline. “A promise ring?”

Cassie takes off the bracelet and hands it to Bobby so he can look at the engraving. “More like a bracelet, but it means the same thing. I’m surprised he didn’t tell you that. You were the one who gave it to me last Christmas.”

The bracelet shines in the sun that betrays the feeling of gloom in the graveyard. Bobby turns it and reads the engraving inside the bracelet . 

‘Who ever loved, that loved not at first sight?’

“Is that Shakespeare?” Bobby asks when he returns it. 

“Yeah,” Cassie says, putting it back on. “We met in English class, we were reading Much Ado About Nothing and had a project on it. We were partnered on it. Got an A plus on it, thanks to Dean. I didn’t understand it at first but he explained it to me so well.”

Bobby laughs softly. “Yeah. He was a smart kid. He built an EMF when he was ten out of an old walkman I had.”

“Is that a hunter thing?” Cassie asks. “Dean explained some of it when he got rid of my, uh, ghost problem a few months ago.”

“He fought a ghost?” Bobby says, shocked that Dean took a risk like that. 

Cassie looks down. “Yeah, some ghost had killed my dad and when Dean found out, he did everything to help solve it. I didn’t believe him at first. I just thought those hunting trips with John were actually hunting trips. When I saw him send the ghost back to hell- or heaven, I can’t really say- well, let’s just say I was shocked.”

Bobby laughs again before looking back at Cassie. “I’m sorry about your dad. Dean didn’t say anything about it.”

“Well, he wanted to keep it a secret. He took me on a couple hunts after that. That camping trip in July was actually a hunt for a werewolf. It only took a day so our plans were saved, thank god.”

Wait,” Bobby puts a hand on Cassie’s shoulder. “He took a day to hunt a werewolf?”

Cassie half smiles, tears forming in her eyes. “Yeah. Why? Is that a while?”

Bobby shakes his head before he lets out a fast breath. “That’s really fast, actually. It normally takes three days minimum.”

“He loved it.” Cassie takes a tissue to dab her eyes. “Just like I love writing. I hope you don’t mind, but is it okay if I go through his things? Just so I can have something of his?”

Bobby nods. “Of course, Cassie. Here, hop in. John and Sam are going to go on a hunt. Apparently it’s a small one but I don’t expect them to be back until Saturday or Sunday.”

“Thanks, Mr. Singer.” Cassie opens the door and jumps in. 

Bobby closes his door and starts the car. “Call me Bobby, Cassie.”

Sioux Falls  
December 25, 2000

Christmas with Bobby was a quiet affair. Mary’s normal constant chatter was gone and John wasn’t here to start a yelling match with Sam like he normally was. Bobby sits in his chair, opening a gift from Mary that she bought before she ‘died.’ 

“Mary always did know what to get me,” Bobby says, turning the book in his hands. He reads the blurb on the back as Sam pulls out the gift he’s been dreading. 

Normally, Sam got the most gifts, next being John, then Uncle Bobby. Mary usually opened her gifts before Sam came down, which was weird but at this point it was tradition. Mary wasn’t here anymore, though, so Sam’s secret gift to her would never be opened. 

“What did she get you, Sam?” 

Sam studies the envelope, wondering what it could be. He opens it to find a few pieces of paper. The first one is a bank statement for a few hundred thousand dollars in his name. He looks up at Bobby quickly. 

“I don’t…” Sam flips to the next page which is a letter. “Should I read it out loud?” 

Bobby nods, tears gathering in his eyes. 

“Sam-

If you’re reading this, that means I’m not here to tell you what this is. I’m probably on a hunt with dad (lame!)

Enclosed is information to access your college fund I set up for you. By the time you read this, there should be enough in it to cover almost all four years (with some financial aid...hopefully).

It may not have seemed like I supported you leaving, I understand why you want to. I hope this helps you get started on doing what you love. try not to forget me while you’re gone, bitch!”

Sam bites his lip to keep from crying. “Bobby, did you know about this?” 

Bobby takes the papers from Sam and looks them over. “Last I checked, this account had almost five thousand. I don’t know how it got to be almost a quarter of a million.”

“This is…” Sam starts to cry. “It’s not fair, Uncle Bobby. She had so much ahead of her and- and-“

“Hey, Sam, it’s gonna be okay.” Bobby gets out of his chair and kneels to hug Sam. Sam cries for a few minutes before a knock sounds at the door. 

Bobby stands up to answer it as Sam wipes his tears away. Cassie stands at the door, her dark hands rubbing together outside of her white coat. “Heya, Bobby.”

“Hey, Cassie, come on in. Turkey is in the oven. We’re finishing up opening gifts.”

Cassie pulls off her coat and takes a couple presents out of her bag. She hands Bobby a bag and takes the box over to Sam. 

“Hi, Sam.” 

Sam stands up. “Hey, Cassie. How are you doing?”

Cassie gives Sam a hug before pulling away to hand him his gift. “Not bad. I hope you don’t mind that I brought you something.”

“Thanks, Cassie.” Sam opens the box to find a Stanford shirt and another envelope. This one looks more official so he quirks a brow at Cassie before opening it. 

“Is this…” Sam falls onto the floor. “Cassie-“

Bobby walks into the room smiling. “What does it say, boy?”

Sam’s mouth opens but no words come out. Cassie laughs and shares a look with Bobby. “Bobby gave it to me when it came a week ago. We wanted it to be a surprise.”

Sam tears up again. “I can’t believe…”

“Not to spoil the moment or anything, but I’m kinda hungry. How about to tell Stanford you’re going while I make us some sandwiches.”

Sam reads the acceptance letter again before picking up the gift Mary gave him. He’s going to Stanford. He’s going to have a chance at a normal life thanks to Mary. He owes her so much. 

Sam sends a quick prayer to God, asking Him to let Mary know that he loves her and to thank her for him. 

Ontario   
December 25, 2000

This was Dean’s first Christmas by himself. After his last meet-up with Crowley to hand over a letter for Sam, Dean drove up to Canada. He crossed into Ontario with nothing to his name besides the Impala and a few hundred dollars in the glovebox, not including the black card Crowley gave him. He vows to never use it unless absolutely necessary because demons can’t be trusted, even if this one has a huge crush on Dean. 

Dean sits back in his chair. The safe-house Crowley gave him was located in Lakeshore, Ontario and he was bored out of his mind. He flipped burgers at the local diner and has a few thousand saved up now. He plans on getting back to the States soon, he just has to find a house. He goes back to the papers he printed for apartments in Detroit and finds a two bedroom one that’s not too bad. He’d need a roommate. He sighs before grabbing his keys. He needs to clear his head. 

As he unlocks the Impala, a voice calls from behind him. “Sweet ride!”

He turns around to find a red-head standing in a Star Wars sweater. “Thanks. Did you want to take a look?”

“Sure!” she bounces over to him and takes a peek into the passenger window. “This is awesome. Are you from around here? Your plates are American.”

He laughs. “Good eye. Yup, I’m from Kansas. I’m trying to find a place in Detroit to move to.”

“Detroit‘s a long way from Kansas, Dorothy.” She smiles at him. “What’s your name?”

“Dean Winchester. And you?”

“Charlie Bradbury. What are you running from, Dean?”

He balks for a moment. “How did you- I mean, why’re you asking?”

“I know a runner when I see one.” Charlie leans on the hood of the car. “Like notices like, and whatnot.”

“Yeah, well, I’ll answer if you do.”

Charlie looks down. “Parents weren’t accepting of me being, well, a dyke for lack of a better word.”

“Lesbian.” Dean says automatically. Charlie looks sharply at him. 

“Yeah.” She says. She crosses her arms. “Now you.”

Dean shifts from one foot to the other. “Abusive piece of shit for a dad. That, and if I ever told him I was a man and not his little girl, I’d probably be in a ditch in the middle of Kansas.”

Charlie smiles. “Looks like we’re two queers in Canada. Let’s go to a bar.”

Dean jumps when Charlie opens the passenger door and climbs in. “What are you doing?”

Charlie leans to talk through the driver side window. “If we’re going to be roommates we need to get to know each other. Now get in! I know a place in Detroit where we can get trashed.”

Dean sighs. “If we’re going to Detroit, I’m not coming back here. Get your stuff. I’ll make the call for the apartment and to quit my job.”

Charlie leaps out of the car. “Let’s do it, Kirk!”

Dean sighs as he watches Charlie almost run to her house across the street. This chick was crazy but Dean almost found it endearing. He locks the car and turns back to the house. Everything was still packed so it will be an easy change. He shifts the papers at the desk until he finds the apartment he was looking at earlier. 

He makes the call to them and then the bank so the deposit can go through. The real estate agent said the place was ready to move in and allowed Dean to move in before the deposit went through. He would get the keys from her tomorrow in Detroit but for now, he and Charlie were owners of an apartment. Someone he met no less than fifteen minutes ago. 

“Son of a bitch.” He chuckles softly before calling the diner. 

“Let’s go, bitch!” Charlie yells from outside the house. Dean laughs and grabs his bags. 

“Coming, dear!” He runs out to the car, leaving a note for Crowley saying thanks. 

“Ready to go?” he asks when he closes the trunk. 

“Beam me up, Scotty!” 

“Jesus Christ.” he laughs. Charlie let’s out a squeal as Dean speeds out of Lakeshore. 

“You didn’t tell me you’re only 18!” Dean sighs as he closes the door to the Impala. 

“The fake should have worked! I made it myself, of course it should have worked!” Charlie sighs. “Rat bastard.”

“You made a fake by yourself?” Dean looks at her in amazement. 

“Yeah,” Charlie sighs again. “It’s an exact replica of my ID. This is bullshit.”

“Anything else you can do, Data?”

Charlie smirks. “Tech genius. Right here.”

“Alright,” Dean says, starting the car. “We don’t have a place to sleep until tomorrow so what do you want to do now?”

Charlie frowns. “If we go down Lafayette there's a park there we can stay. A graveyard is down there as well, if you’re down to sleep there. No one will bother us there.”

Dean shoots Charlie a look of disbelief. “Why not?”

Charlie smiles. “Great! Can’t wait to get to know you over a couple of tombstones.”

Dean shakes his head. “You’re one crazy butch, huh?”

“Says the person with an array of weapons in his trunk.”

“You leave Baby’s trunk alone. I’ll explain that when we get to our place of rest.”

“You named your car?” Charlie rolls the window down to let in the night air. 

“She is my pride and joy. Yes she has a name.” Dean rubs a hand across the dashboard. “A great name, huh, Baby?”

Charlie laughs as they speed down the streets. “So, you’re transgender, huh?”

“Yup.” Dean pops the ‘p’ at the end. “And?”

“Nothing,” she says quickly. “I was just wondering if you’ve taken T yet. My friend's cousin's boyfriend’s uncle is trans and he has a shit ton of testosterone he’s supposed to take. He doesn’t anymore, something about microchips from Russia or something. The guy’s crazy.”

“Testosterone? No, I don’t take any.” Dean pauses. “Do you think that uncle will give it to me?”

Charlie shrugs. “Can’t hurt to ask. He lives near my mom’s old house in Farmington Hills.”

“Okay,” Dean revs the engine. “We’ll visit them tomorrow before we meet Maggie at her office.”

“Sounds like a plan, bitch.” 

Dean smiles. “Anything else you need, Red?”

“Something to eat, I’m starving!”

They laugh as Charlie’s stomach growls. “You’re paying.”

Charlie gasps in shock. “What about chivalry?”

“I don’t put out before the first date.” Dean glances at her. “After dinner, sure, why not?”

Charlie shoves Dean’s arm causing them to swerve. “Bitch!”

Dean laughs as he looks around for something open at 10pm. 

January 24, 2001

Bobby sits alone at the table with a plate of leftovers. Sam left for school at eight and it’s just about lunchtime for Bobby. He turns on the 2pm soaps and gets ready to eat. His phone rings just as he lifts up his fork for a bite. Grumbling, Bobby answers the phone. 

“‘lo?”

“Heya, Bobby. It’s Dean.”

Bobby almost drops the phone. “Dean?” 

“Yeah,” there’s a pause. “It’s a crazy fudging story, but I faked my own death.”

Bobby falls to the floor. “We buried you.” 

“I know.” Dean clears his throat. “I’m safe. I have an apartment and a job now so I got steady income. I wanted to call and let you know. That I’m, uh, alright and stuff.”

“That’s good.” Bobby looks up at the ceiling. “Cassie left. Said she couldn’t handle living somewhere with sad memories.”

Dean sighs. The line grumbles a bit while no one talks. “I sent her a letter. That’s why she left. I told her everything about John. She visited me for a few days before leaving. She’s got a position at the Washington Post.”

“You wrote her a letter but didn’t contact us at all?” Bobby says slowly. He's mad. Didn’t hear do everything for Dean?

“I wanted to.” Dean rushes out. “I really did. I couldn’t do that, though. I would have to tell Sam everything and he doesn’t need that on his plate.”

“And your death? He needed that on his plate?”

“Bobby, it was a stupid move. I get it.” Dean growls at him. “Don’t you think I regret ever agreeing with that fucking demon. I was selfish. I just wanted it to end.”

“Dean, that’s not-“

“No, Bobby,” Dean shouts. “I could have waited! Once Sam left for college I could have left with him or- or- or literally anything else!”

“Dean, you’re not selfish for making a better life for yourself. That’s human nature.” Bobby stands up again, dragging a chair near the phone. 

“I should’ve been better. That’s why dad hit me. I was never good enough, I should have stayed to learn my lesson.”

“No you shouldn’t.” Bobby yells back. “You’re the best kid anyone could have asked for. You grew up too fast to take care of your brother and father. You deserve to be selfish.” 

“Bobby, I can’t come back.” 

Bobby sighs. “I know. I understand.”

“No, you don’t get it.” Dean pauses. “My roommate found someone who can supply testosterone so I can fully transition. I can’t ever be that girl you knew before.”

“You just have to be you, Dean.” Bobby tears up. “That’s all you have to be. Is this Testosterone dangerous?”

“Not really,” Dean says. “It will help me look more like a man. I’ll come back in a few months.”

“How will I introduce you to Sam?”

“I’m your nephew from Detroit. I’m visiting for the summer with my roommate, Charlie. We’ll get a hotel room when we come down. Probably for Sam’s birthday, I’m not sure.”

Bobby sighs. “You and Sam both know I’m an only child, idjit.”

“Your wife wasn’t.” Bobby freezes. “Look, I’ll fake a name, it’ll be fine. Sam will be too preoccupied with getting ready for college so he won’t notice.”

Bobby lets out a hard breath. “You’re an idiot, Dean.”

“It’ll be fine,” Dean says. “Charlie will make us ID’s so it’ll be legit.”

“Your roommate can make fake ID’s?” 

Dean laughs. “She can. She just doesn’t know how to use them. We’ll plan for May 2nd, okay?”

“Alright, son. I’ll tell Sam when he gets home.”

“Tell me what?”

Bobby jumps a foot in the air. “Jesus, Sam. Dean, I have to go, I’ll talk to you later.”

“Bye Bobby.” Dean pauses. “Make sure Sammy knows I’m proud of him.”

“Will do. Take care.” Bobby hangs up and looks at Sam. “Dean is coming to visit us sometime in May.”

Sam sets his bag down at the table. “Dean who?”

“Apparently a nephew of mine.” Bobby sits down with his food again. “He called out of nowhere saying he was left with my phone number.”

“Is he staying for good?” Sam pulls out his work. 

“Not sure.” Bobby takes a forkful of rice. “Didn’t say. I assume he’ll leave after a while but he wanted to connect. After my wife died, her family cut me off.”

Sam nods. A few moments pass before Sam asks, “Did dad call?”

Bobby takes a deep breath in. “Nah. No word from him yet. He’ll be back soon, though.”

Sam nods again. “I think I’ll visit Mary later if you want to come.”

Bobby nods. “Sure, kid. Gonna wish her a happy birthday?”

“Yeah,” Sam chokes. “She’d be twenty-two.”

“We’ll get some nicer flowers for her today, okay?” Bobby picks up his half finished plate and messes up Sam’s hair with his free hand. “Now finish your work! You don’t want Stanford to reject you for poor grades your last semester.”

“Thanks, Uncle Bobby.”

“No problem,” he said. He didn’t finish his food, his appetite gone with the knowledge of Dean being alive and having to keep that from Sam. Hopefully Dean explains it to Sam when he comes, because Bobby is not looking foreword to that conversation.


	6. Benny is here!!! But for how long? ; )

April 29, 2001

“Dean, seriously, the stubble is not going to magically fall off in the shower.” Charlie calls from the couch. 

“I’ll shower in a second.” Dean grumbles, whipping up some quick soup for lunch. “I’m a working man, I’ll shower when I want.”

“You fucking stink, Jaba.” Charlie changes the channel on the TV. 

Dean peaks out of the kitchen, wooden spoon pointing at Charlie. “You take that back. I’m Han fucking Solo and you know it, bitch.”

Charlie raises her eyebrows and looks away from Dean. “Smelling like Chewbacca more than ever, though.” 

Dean huffs and turns back to the pot of tomato and rice soup. “See if I share any of my food with you ever again, your highness.”

“Dean,” Charlie shoots up off the couch. “Don’t even joke about that.”

Dean laughs and grabs a couple paper bowls for both of them. “I won’t leave your worthless ass to starve. Now come over here and help me make some grilled cheeses.”

Charlie turns off the T.V. and heads to the fridge. “Are you excited to see your family again?”

Dean sighs. “Is it bad if I say not really?”

Charlie hands Dean a couple slices of cheese. “No, if anything I think that’s alright given the circumstances.”

“John is going to be there.”

Charlie nods, waiting to see if he’ll say more. Dean flips the sandwich in the pan and the sizzle fills the silence. 

“I don’t know if I’ll be able to say no to anything he says.” He scoops the sandwich onto a plate. “Do I even look that different? My voice just went down in pitch, but will he still recognize it?”

Charlie places a hand on Dean’s forearm. “It’ll be okay, Dean. If it gets to be too much, we can leave. He can’t stop you from living your life, especially after what he did.”

Dean nods and takes a shaky breath in. “I just want him to be proud of me. I was never good enough for him, you know? Even when…” Dean pushes his fist into the counter. “There was always something wrong, you know?”

Charlie hugs Dean. “You’re perfect to me, Dean Winchester. And don’t you forget it.”

Dean nods and hugs her back quickly. “Alright, enough with the heart to heart, that filled my yearly quota.”

Charlie laughs. “Make me a sandwich, peasant. I’ll turn on something to watch unless you want to read Harry Potter together.”

“No spoilers!” Dean yells over his shoulder as Charlie walks out of the kitchen. “I haven’t read the fourth one yet!”

“Neville makes out with Harry and Hermione officiates their wedding!”

“You bitch!” He throws a towel at her as she laughs away. He chuckles to himself before turning back to the stove. He’s not ready to see John again but, goddamnit, he’s ready to see Sammy again even if it’s last time. 

May 1, 2001

Sam is laughing with Bobby when a knock sounds at the door. 

“That must be dad.” Sam sighs. Bobby stands up a little too quickly. 

“I’ll get it.” Bobby rushes towards the door and Sam turns to look towards the front of the house. 

The door opens and Sam can hear voices. He stands slowly before meandering towards the door as quietly as he can. There’s a flash of red hair before he hears the voices clearly. 

“Bobby, this is Charlie Bradbury. Charlie, this is my Uncle Bobby.” A gravelly voice says. 

“Pleased to meet you.” The feminine voice says. 

“Well, come on in. We’re waiting for John to come back. Tomorrow is Sam’s birthday so we were going to just get a cake tonight because Sam will be out with his friends tomorrow.”

Bobby walks into the hallway where Sam is. The man next to the redhead comes to view last. 

“Dean, let me introduce you to Sam.” Bobby gestures to Sam. “Sam, this is Dean Bradbury, my nephew on my wife’s side.”

Dean stares at Sam for a second before being nudged by the woman. He jumps for a second before sticking out his hand. “Nice to meet you, Sam.” he says gruffly. 

“And this is his sister, Charlie.”

“Hi, Sam!” She shakes Sam’s hand as well. “I heard you got into Stanford. That’s pretty stellar.”

“Thanks, Charlie.” he looks at Bobby. “I thought your wife’s family doesn’t talk to you anymore.” 

“Well, after Aunt Karen died, our family cut off all ties with Uncle Bobby.” Charlie loops an arm around Dean’s. “Dean here wanted to find out what happened to her so he started hunting for information. That led us here, where we figured out demons were real.”

“We’re hunters.” Dean says. 

“Yup!” Charlie looks at Sam. “We were on a case nearby and decided to visit the man we’ve been talking to these past few months.”

“Huh,” Sam says. 

Bobby shoots a look at Dean. “Yup. I’ll show them around the Yard while you finish up your work. John should be back soon.”

Charlie nudges Dean towards the back door. “Right, well, let’s go check it out. Dean?”

“Yeah, uh,” Dean stumbles out of the back door. “Yup!”

Sam raises an eyebrow and looks back to his work. Weirdos. 

Dean falls to the floor, ass first. Charlie tries catching him but ends up sprawled on top of him. 

“Jesus, you idjits.” Bobby helps them stand up. “Can you be more suspicious?”

“Sorry,” Dean lets out a sharp breath. “It’s just…”

Charlie wraps an arm around his waist. “A lot?”

“Yeah.”

Bobby nods. “So, Dean, did you want to see the remnants of the Impala?”

“It’s not Dad’s car,” Dean says, taking Charlie’s hand. “It’s a fake Crowley set up for me. I have the real one with me.”

Bobby gives Dean a look. 

“Well, not now, obviously. We took a cab here. But it’s back at the hotel.”

“Well, I’m going to give you this one. You can take the trailer to carry it back to- what was it? Detroit?”

“Thanks, Bobby.” 

“Yeah, thank you for being so cool, Mr. Singer.” Charlie says. “Not a lot of people we know are as cool about this.”

“Not everyone is a hunter.” Bobby says. “Here, help me move this onto the trailer. I’ll drop you kids off at the hotel after dinner.”

“Is John going to be there?” Dean asks softly. 

Bobby sighs and looks down. “Yeah, maybe. He’s supposed to come back from a hunt today or tomorrow.”

“If it’s tomorrow,” Charlie says. “I hope you don’t mind us not being here longer. Obviously if it’s tonight, we’ll try to leave early.”

“No, Charlie, it’s okay.” Dean says. “I can handle this. If he comes tonight, we’ll stay for as long as we can. We leave tomorrow, anyway. I only took until Thursday off.”

“A real job?” Bobby asks. “What are you doing?”

“I’m at a mechanic just outside Detroit. It’s good pay and it’s something I know how to do.”

“He’s amazing.” Charlie gushes. “He can make any car start, even the trashed ones.”

“Well, not every car.” Dean blushes. “There’s a few I can’t fix at all. I'm not the best, but I'm not the worst.”

“Well, you fixed that old Ford truck with Sam a few years back. I couldn’t get that thing to start for years.”

“That was mostly Sam,” Dean shrugs. “It’s not like I did a lot of work.”

Charlie slaps Dean's shoulder. “Stop being so modest! Take the compliment, Dean.”

Dean chuckles. “Fine, whatever.”

The three of them go back inside. John doesn’t come back that night so when Bobby drives the two of them back to the hotel, Dean hands Bobby a gift for Sam tomorrow. 

“I bought myself one so I feel like Sam needs to have this.” He puts his hands in his pockets. “It’s my old switchblade. I have a better one now; one with a new engraving.”

Bobby peeks inside the newspaper it’s wrapped in. “Who do I tell Sam it’s from?”

Dean shrugs and looks down. “Just say it’s from you. I’ll get him something for Christmas.”

Bobby frowns. “Are you going to tell Sam about…” He gestures to Dean. 

Dean shakes his head. “Not yet, anyway.”

Bobby sighs. “You’re going to have to tell him.”

“I know.” Dean looks at Charlie, who just came out of the bathroom. “I’ll do it soon.”

November 2, 2005

“I’m glad your Uncle is coming to visit us for Christmas, Sam.” Jess says as they walk back to their apartment. “It’s a big occasion, I know my parents are coming.”

“Yeah, well, I just wished my sister could have seen this.” Sam says, pulling out his keys, Mary’s old switchblade is his keychain. “Without her, I don’t think I would’ve been here to see this or meet you.” 

Jess smiles softly. “I’m sure she’s watching from heaven.”

“I think she is.” Sam opens the door for them. “I’m sure she would have liked you and approved of you becoming my future wife, Jess.”

She smiles again and kisses his cheek. “Alright, enough sap from you, Pine Tree. I’m going to bed if you want to join me.” She winks and starts up the stairs. 

Sam laughs and catches up to her, taking her in his arms before heading to their room number. 

Sam wakes up to something dripping on his face. He blinks awake and touches his cheek, pulling his hand back to see blood. He looks next to him and finds the bed empty. 

“Sam!” Jess screams from above him before bursting into flames. 

“Sammy!” A voice yells from the hallway. Dean comes into view while Sam screams. “We gotta go!”

“Jess!” Sam tries to reach her but Dean grabs him and forces him to leave the room and Jessica behind. 

Outside the building, Charlie is on the phone with the fire department. “And please, hurry. I think there’s someone still in the building.”

Dean lays Sam on the floor as the building residents finish coming out of the building. “You okay? You’re not hurt, right?”

“Jessica!” Sam says, trying to stand up. “She’s still in there. We have to get her, Dean, please.”

Dean watches as a tear falls down his face. “Sam, I don’t think-“

“Please.” Sam begs. 

Dean looks at Charlie while she gives him the “don’t do anything stupid, Winchester” look she’s perfected over the years. “You see if you can find where the bastard is. I’ll be right back.”

Dean sprints towards the burning building as people cry out for him to stop. Inside, he makes his way to Sam’s apartment number and rushes inside. He knows Jessica is dead. He saw Azazel kill her before sticking her to the ceiling. He was too late for her, but he can get her body out for Sam. 

He finds her sprawled on the burning bed, half her body on fire. Dean coughs at the stench and tries to choke the fire off of her body. He picks her up and runs out, picking up a few photo albums as well. Firefighters are at the front door of the building with oxygen masks for Dean when he gets there. one of them rushes to Jessica’s body but Dean shakes his head. 

“She’s…” he coughs. “She’s gone.”

A police officer comes up to him when the fire is out and Jessica’s body is on the way to the morgue. “Did you see anything out of the ordinary?”

Dean coughs to cover up him thinking of something to say. “I saw a guy run out of my brothers apartment when I was coming to surprise him.”

“Can you describe what he looked like?” The officer took out a notebook and a pen. 

“Blonde hair, red shirt, uh, pretty tall. Maybe about 6’2”? Dean shrugged. “He pushed me out of the way before heading out the back door. I thought it was weird so I ran in and saw my brother passed out on the bed next to his girlfriend who was stabbed in the stomach. The room was on fire so I checked for a pulse on Jess before grabbing Sam and running out.”

“Thank you, sir.” She says. “This is good. I’ll keep you and your brother updated on how the case goes.”

“Thanks.” She walks away and Dean heads over to Charlie and Sam. 

“Do you think it was Azazel?” Charlie asks. 

“No.” Dean says. He takes the keys out of his pocket before heading to the drivers side door. “It looks like his MO but the guy didn’t have yellow eyes. Must have been a lackey or something.”

Charlie nods and looks at Sam. “C’mon, big guy. We need to get you to our hotel room before the shock sets in.”

She pushes Sam into the backseat and closes the door. He passes out before Dean can start the car. 

“Should I ask him to join us?” Dean asks as they drive off. “He got his degree and is interning with some hotshot lawyer. I don’t want to ruin his life.”

“It’s up to him.” Charlie says. She looks back at Sam’s sleeping face. “He just lost his partner, he’ll be grieving for a while. After that, well, it’s up to him.”

The two sit in silence until they reach the hotel. “You know,” Dean starts. He takes a breath in. “Sam’s not a runner. He faces his problems head on. Hec won’t stop until we kill that son of a bitch.”

“If he sticks around that long,” Charlie opens her door. “You’re going to have to tell him the truth.”

Dean nods before getting out of the Impala. He’ll have to do it soon. 

Between the two of them, Charlie and Dean maneuver Sam onto one of the two beds in the room. 

“I’ll take the couch.” Dean says. 

“We can share, bitch.” Charlie throws a pillow at Dean. “We’ve shared women before.”

“Hey,” Dean points at her. “We swore to never talk about the Francine Incident of ‘03.”

Charlie holds up her hands. “I’m just saying-!”

Dean smirks and takes off his make-shift binder. “I’m on the right side.”

“Yes, yes. We’ve gone through this before.” Charlie hops on the left side. “You’re also a ‘big spoon’ until you fall asleep.”

“Damn right.” Dean settles on his stomach before pulling Charlie closer to himself. “I’ll grab us breakfast tomorrow when I get up.”

“Thanks, bitch.” Charlie yawns. “Sam will be okay, right?”

“He always is,” Dean closes his eyes. “He’ll bounce back. It will take a while. Losing the love of your life is a Winchester rite of passage at this point. I just wish I could’ve gotten to know her more, you know?”

Charlie makes a sound of affirmation. “Be the big brother you never really got to be, right?”

“Yeah.” Dean snuggles closer to Charlie. “I’ll tell him soon. I just need to get my thoughts together.” 

“Take your time.” Charlie yawns again. “You have time.”

Dean nods before tucking his face in Charlie’s shoulder. He’ll tell him. 

July 21, 2006

Charlie was at ComicCon and Sam was up north having some type of memorial for Jess’s birthday so he went on a hunt alone. 

He thought it was a small nest of vampires but it turned out to be a serial killer. He located the guy and gave him to the cops within a day. Overall, it was a small trip and took about two days. The only thing that lengthened his stay in the nearby city of Lafayette was a guy named Benny. 

“You’re a vampire?” Dean asks, machete in one hand with his gun trained on him with the other.

“Yeah,” Benny answered. “But I ain’t hurting anyone.”

Dean chuckles. “Yeah, right.”

“It’s true!” Benny takes a slow step forward. “I’ve rotted in Purgatory for nearly fifty years, boy. I don’t care to go back so soon.”

Dean licked his teeth in his closed mouth, debating what to do. “Why are you here, then?”

“I live a little ways north from here. Carencro. I’m trying to find the one that turned me so I can kill him.”

“And do I know if you’re lying or not?”

Benny freezes. “I guess you just gotta trust me.”

Dean stares at him for a few minutes, neither one of them moving a muscle. After about six minutes, Dean slowly lowers his weapons. “What have you got?”

“You’re gonna help me,” Benny says in disbelief. “Didn't think that would work.”

“Yeah, well, if someone is turning people, I gotta take care of them.” Dean places the gun in his waistband. “I’ll take care of you after.”

“Even after I help you take down a big guy,” Benny says, walking towards Dean. “You’re still going to kill me?” 

“‘All monsters are abominations.’” Dean recites from memories of John beating it into his memory. “Rule numero uno for hunters. It’s not personal, man.”

“Name’s Benny.” he says. “If that helps you understand that I’m alive and have a life.”

Dean laughs. “Just because you have a name don’t make you human.”

Benny shrugs. “If he walks on two feet…”

Dean shakes his head. “Tell me what you got on your big kahuna?”

“Not much.” Benny reaches into his back pocket for a small folded up piece of paper. Dean raises his machete. “Come on, brother. I thought we just talked about it.”

“Force of habit.”

“Hmm.” Benny opens the paper and hands it to Dean. “He’s known as the Old Man. He turned back in the 50’s. I tried saving my girl at the time, Andrea, but he killed her. The town blamed it on me so I had to book it out of there. I’ve been in Scotland until a few weeks ago. The Old Man took over Andrea’s property so that’s where I was heading before you decided to gank me.”

Dean nods. “I’m not sorry about that, but I’m sure we can go and kill the guy tomorrow. For the rest of tonight, we gear up.”

Benny nods. “We’ll make a great team when you decide to not kill me, brother.”

“Yeah, sure.” Dean laughs. He folds the paper again and starts out the door. 

August 2, 2006

“Dean, are you stupid?” Sam yells at him from across the table. Charlie and Benny were outside the room, trying not to listen in. “A vampire? It’s going to go rogue and kill us all!”

“Chill out, Sam.” Dean slams a hand onto the table. “I will personally chop his fucking head off of the time comes!”

“‘If’ is a good start,” Benny whispers to Charlie. “Between you and me, kid, me and Dean already consummated this marriage if you catch my drift.”

Charlie scrunches her face in disgust. “Gross. He’s like my brother.”

Benny shrugs. “Sam will have to kill me to get me to leave. I can’t willingly leave Dean. He’s such a great lay.”

Charlie covers her ears. “Please stop.”

“Dean, are you crazy?” Sam takes a deep breath in. “You’re always the one saying monsters don’t have any humanity- that they all should be killed! And, what, this one vampire is the exception?”

Dean sighs and falls back into his chair. “He’s not the only one, but he’s the first. If you don’t like it, then leave. School’s starting back up soon, anyway. Charlie and I will keep an eye on him, alright?”

Sam sighs and pinches his nose. “Dean, I’m not your brother, but I do care for you like one. Just be safe, okay?”

“Yeah,” Dean’s voice cracks. “I understand.”

May 1, 2007

Dean holds Sam as he dies in his arms. “Sammy?” Dean asks shakily. “Sam?”

Sam doesn’t answer. 

Dean starts to cry. He never told him. Charlie said this would happen. Benny said this would happen. Fuck!

“You’ll be too late if you don’t tell him now.” She said a few months ago when picking for a convention. “Something will happen and you’ll miss your chance.”

“Psh,” Dean scoffed. “I have plenty of time.”

He didn’t. 

The next day brought Dean to a crossroad. He summoned a demon to make a deal. 

“Darling!” the voice called out. “It’s been too long!” 

Dean turned to find Crowley standing against the Impala. “Hello, Crowley.”

Crowley walks over and circles Dean. “My, you’re looking manlier than ever. That red head site knows her stuff, eh?”

“Crowley-“

“Nuh uh! Let me take a guess.” Crowley puts a finger to his chin. “You want me to raise Sam from the dead.”

Dean nods. 

“You do know that’s going to quicken the count on the hounds for you, right?”

“I know.” Dean says. “Just do it.” Dean sighs. “Please.”

Crowley nods and snaps. “Very well. Moose over there should wake up in a few minutes. I’ll see you in a year or so.Tah, Squirrel.”

Crowley vanishes and Dean runs back to the car. In the back seat, Sam starts to wake up. 

“Hey, buddy.” Dean says, relieved as all hell. “Welcome back.”

“Dean?” San asks groggily.

“I’m here, kid.” Dean says, handing Sam a water bottle. “Let’s get back to Charlie now, eh? Think she has the Lord of the Rings rented from Blockbuster. We’ll watch that tonight, okay?”

Sam nods before passing out again. Dean sighs as he moves to the driver's seat. 

Dean has a deadline now. He’ll tell Sam soon. 

August 12, 2007

Benny strokes Dean back as they lay together in bed. “You still haven’t told him.”

“Told who what?” Dean grumbles, tightening his arm around Benny’s chest. 

“About us, for one.” Benny kisses the top of Dean’s head. “And about who you are, for two.”

Dean groans. “I don’t think Sam understands pretty much anything in my life right now.”

“Then explain it to him.” Benny moves a hand to make Dean look at him. “I don’t understand what’s holding you back.”

“What if…” Dean swallows hard. “I just…”

“What if your brother turns into your dad?” Benny raises a half smile on his face. “From what you’ve told me of your dad, Sam is the exact opposite.”

“Yeah, well, this might be different.” 

Benny sighs and looks at the ceiling. “Cher, I don’t know what you’re going through, but it can’t be worse than when I first offered to go down on you.”

Dean covers his face with his hands and rolls off Benny. “Don’t fucking remind me, Benjamin!” 

Benny rolls on top of him and nuzzles into Dean’s neck. “Don’t call me ‘Benjamin,’ dick!”

Dean and Benny laugh for a while, rolling in the sheets under the sunlight peeking in through the window of their room. 

A knock sounds on the door. “Dean? You in there?”

Dean shoots out of the bed and sprints towards the bathroom. “I’m getting in the shower! Come back later!”

Sam scoffs. “Dean, I am a man who grew up in locker rooms, I’ve seen dicks before. I have a break on the case.”

Dean tries to shoo Benny out the window of the second floor room. Benny shoots Dean an incredulous look. 

“I may be dead,” Benny whispers, shimmying into his shirt as he heads to the window. “But I still can break my neck!”

Dean gives him a quick kiss. “See you later, Benny.”

“Fuck you.” he smiles and jumps out the window. 

Dean quickly wraps a towel around himself and looks for the wrap he uses to bind. “One second, let me grab clothes and you can talk to me through the bathroom door, perv.”

Sam sighs loudly from behind the door. “Open the door, Dean.”

Dean unlocks it and sprints back to the bathroom. Sam opens the door to get a glimpse of Dean’s bare ass for a millisecond and yells, “My eyes! Jesus, Bradbury, do you even see the sun?”

“Shut up, bitch! You love it!”

Sam sits next to the bathroom door. “So get this, the lady we interviewed yesterday about the ghost was the dead guy’s aunt. Apparently, she threatened to kill the guy on multiple occasions because he dressed like a woman.”

Dean’s blood freezes while the shower splashes on his back. “Oh? Was it a kink type of thing or a lifestyle?”

“His friends said he wanted to be a woman. He apparently was going to get some meds to fuck with his body so he can look the part. The majority of them said they supported his, uh, ‘transition’ but one of them agreed with the aint.”

“And, uh,” Dean scrubs the bar of soap into his hair. “What do you think? Friend who didn’t support her  
killed her and she haunts her aunt?”

“Her?” Sam asks. “This is a guy, Dean.”

Dean turns off the shower. He feels like he’s going to throw up. He wishes Benny was here. “From what you’ve told me, it seems like she was trying not to be a guy.”

Sam scoffs. “Yeah, well, my dad always told us that gay men would dress as women so they can screw kids or some shit. I don’t have good examples of them.”

Dean tightens his bandages and stares at himself in the mirror. He studies the feminine way his eyes are and how his lips are more womanly than any man’s. He starts seeing his old body, the one John violated over and over again. He takes a deep breath in. “Yeah, well, I did too. Dad always said gay people were another type of monster that needs to be exterminated.”

“Exactly,” Sam says. He closes the notebook and stands. “Well, I should say gay people don’t bother me as much anymore. Some people at Stanford that I know are gay- or, well, gay-curious. They’re nice people.” 

Dean nods and puts on the layers he always wears. “I need to call Charlie before we go check out this friend. I’ll meet you by Baby in a second.”

Sam laughs. “Go ahead. See if she can come down, we might need her to talk to the aunt.”

“Sounds good.” Dean listens to Sam’s footsteps leave the room. The door clicks shit and Dean finally throws up. 

“So Sam is transphobic?” Charlie asks over the phone after Dean’s freak-out. 

“I mean, I guess.” Dean sighs and lays back in the messed up bed. “He didn’t call her a tranny so that’s a fucking plus. John basically said that we needed to be extinct if that helps.”

Charlie sighs. “Dean, John is a fucking demon. I don’t care if he isn’t a physical demon, he is the literal worst.”

“Yeah, you say it.” Dean flips open the Hunter’s Journal. “But hearing Sam completely ignore her last wishes of being a woman hurts, you know?”

“Not really, but I can only imagine.” The line is silent for a bit. “Not to make any excuses for Sam, but I’m sure that if he knows more about being trans, he’ll accept you.”

Dean sighs welty, tears gathering in his eyes. “Is it bad that I just want to sit with Benny for a while and try to forget this ever happened?”

“Honestly? I don’t blame you.” Charlie flips pages in her notebook. “I can probably come down tomorrow to help with the case. You can take the rest of the week with Benny and I can tell Sam you’re on a bender.”

“Charlie, if you weren’t gay and I wasn’t a taken man, I’d marry you.”

“That’s not out of the question,” Charlie says. “But Sam will ask why you’re marrying your sister and then you’ll have to explain it to him so…”

“You’re right,” Dean sighs. “Okay, I have to go now. I’m in room 32 and Sam’s across the hall. Benny is around here, somewhere. He stayed over last night.”

“We get it, you can get some while I wallow in the desert.”

Dean laughs. “See you soon, Charles.”

“Bye, bitch.”

Dean hangs up and punches the bed before he stands. “Fuck.”

He walks out the door to his Baby. “You ready to go, Sammy?”

Sam nods and opens the passenger door. “Still can’t believe Bobby gave you the Impala my dad lost.”

“What can I say,” Dean says, revving the engine. “I was able to fix her so I get to keep her.”

Sam laughs and shakes his head. “We’ll visit the friends first. Kimberly Slater, Terrance Oscarlee, and Hannah Arbeit. They’re the ones okay with the ghosts lifestyle. I think Hannah was the one who was closest to him.”

Dean nods and speeds along the road towards Hannah’s house. 

“Hannah, what exactly happened to Shawn?” Sam asks, concern edging his voice. 

“Well,” she starts. “Shawn wanted to be called Samantha, so please be courteous of her last wish.”

“Of course,” Dean says, shooting Sam a glare. “Can you tell us about how she died?”

Hannah’s eyes tear up. “She was stabbed next me while we were waiting for a cab a year ago.”

Dean sadly nods. “I’m very sorry for your loss.”

Hannah sniffles. “Thank you.”

“Miss Arbeit,” Sam leans forward. “Can you tell us about anything strange that happened that night?”

Hannah leaned back on the sofa. “Well, the coroner found a small bag in her purse after it happened. it was filled with small bones and flowers. But Samantha was known to have small bags with flowers in it. She collected them.” 

“Agent Smith,” Dean addressed Sam. “Do you mind if I talk with Hannah alone for a moment?”

“Sure,” Sam said. “I have to use the bathroom, anyway, if you don’t mind.”

“Not at all,” Hannah pointed down the hallway. “First door on your right.”

“Thanks.”  
Sam stood and left. Dean waited for the door to close before he leaned forward. “This doesn’t involve Samantha’s case, but I was wondering how she came out to you as trans?”

Hannah’s eyebrows shot up. “Oh, well, she was over one day and while I was trying in dresses for homecoming, she told me she always wanted to wear a dress. We were the same size so I let her try mine on. When she saw herself in the mirror she broke down. It took awhile but she finally told me how she felt like a woman and not a boy.”

Dean nods. “I see.”

Dean shifts his weight under Hannah’s gaze. “What?”

Hannah gives Dean a small smile. “Are you…?”

Dean nods. “Don’t tell anyone, alright? I haven’t figured out how to tell anyone.”

Hannah smiles. “It’s hard, at first. Samantha lost a lot of people when she came out. That’s why she moved here. Her family disowned her.”

Dean nods again. “Thank you. We’ll solve her case.”

The bathroom door opens as Hannah gives Dean her thanks. “Ready to go, Agent Halen?”

Dean nods and stands, offering a hand to Hannah. “Thank you for your time, contact us if anything comes to mind.”

“Will do, agents.”

In the Impala, Sam looks out the window. “So this dude died a year ago, seemingly stabbed to death with no one around and a baggie of spell ingredients in it. A few weeks ago, the guy’s aunt reports that he’s haunting her house. I don’t get it.”

“Yup,” Dean thrums his fingers against the wheel. “Demon is out. Samantha has no earthly possession she was tied to so that means we have to find out who killed her.”

“My bet is on the friend, Anthony Johnson. He was the one who was ranting about how Shawn deserved what he got.”

“Samantha.” 

“What?” Sam looks over at Dean who has a death grip on the wheel. 

“Her name is Samantha, Sam. You’ve been reminded multiple times to call her Samantha and not her old name.”

“Sorry, I forgot.” Sam shrugs. “It doesn’t really matter, though, because he’s dead!”

“Yeah, Sam,” Dean glares at Sam. “It does matter. She tried her whole life to be who she knew she was and within a couple seconds, you erase everything she built for herself.” Dean pulls into a parking space and gets out. “I’m leaving. I can’t deal with this if you’re going to be like that.”

“Like what, Dean?” Sam us confused. He gets out of the car and watches Dean almost run to his room. He sighs. 

“Sam?”

Sam turns to see Benny heading up to the motel entrance. “Benny?”

“Hey, brother.” Benny smiles. “I was in the area and I remember Dean saying he was gonna be here.”

“Uh, yeah, Benny, he’s here. He’s packing though. I think I made him upset but I don’t know how.” 

Benny nods. “I’ll see if I can calm him down.”

“Thanks, man.” Sam points up to the second floor. “He’s in room 32. Go ahead and knock, I’ll be across the hall.”

Benny nods and meanders back to Dean’s room. When he gets there, he can hear Dean sobbing. 

Benny knocks gently. “Dean? It’s Benny.”

There’s shuffling on the other side of the door before it opens. Dean stands there in his rumpled suit with snot covering his face. “He won’t accept who I am, Ben.”

Benny closes the door before taking Dean in his arms. “What the hell are you talking about?”

Dean takes a deep breath in, trying to push down the hurt he feels. “We’re in this ghost case. She's haunting her transphobic aunt. Samantha died a year ago and people suspected her aunt did it. No one can prove it. ‘m pretty sure the aunt is some type of witch or psychotic bitch. They found a small bag- like a hex bag- on Samantha during the autopsy.” 

“Not to sound like a monster, cher,” Benny holds Dean tighter. “But this doesn’t sound like something nearly as bad as it could have been.”

“Sam won’t call her by her chosen name.” Dean tightens his hold for a second before stepping back. “He refuses to call her a woman, even after he’s been asked multiple times.”

“Have you tried explaining what being transgender is?” Benny asks, folding his arms together. “Or did you just lose your temper and run?”

Dean looks down. “It’s not that hard to do something a dying person asked.”

“Dean,” Benny takes a step forward. “Explain it to him.”

“How?”

“Just like you did to me.”

Dean laughs softly. “I’m not going to say, ‘Sorry I don’t have a dick but you can still suck me dry’ to my own brother.”

Benny smiles. “Then tell him how you feel, you repressed cowboy.”

Dean frowns. “It’s not that easy.”

A knock sounds at the door. “Dean? Benny?”

Dean sighs. “I don’t know how-“

“Don’t think, cher.” Benny opens the door. “Sam, great of you to join us. Can I try explaining why Dean is upset?”

“Go ahead.” Sam crosses his arms. 

“Your ghost, Samantha,” Benny sits down on the freshly made bed. “Is a murdered trans woman. She was killed by her transphobic aunt who seems to be a witch.”

Sam raises his eyebrows. “I thought it was his friend not his aunt.”

“See?” Benny points at Sam and looks at Dean. “Right there! You keep referring to Samantha as a man. She is a woman!”

Sam’s brows furrow. “But he has a dick.”

“No, brother,” Benny punches his nose. “She may have a dick but that’s not what decides her gender. She most likely felt like a woman so she decided to become one to make herself happy.”

“Sam,” Dean says, voice rough. “It hurts knowing that you won’t take the time to do something someone wanted. You may not understand it, but it’s very important to me that you allow people to make their own choices and to respect them.”

Sam looks down. “I didn’t know it was that serious. I just thought it was some type of drag queen thing.”

“Well, it’s not, Sam.” Dean takes a deep breath. “I’m trans, so if that changes your perception of me, then fuck you.”

Sam leans against the wall. “What?”

Dean looks at Benny who gives him a nod of support. “I’m transgender. I was a woman but now I’m a man. I’m still Dean. I’m not her anymore; she wasn’t who I was. So it hurts when I see you just ignoring someone like me.”

Sam doesn’t know what to say. “I’m...I’m sorry, Dean, I didn’t know. I’ll try to be better.”

“Please do,” Dean says. “Charlie is coming tomorrow, she’ll take my room. I need some space from this.”

Sam nods. “Yeah, of course, Dean. It must be hard to see this happen.”

Dean nods. “I’m going to Bobby’s. I’ll take Benny with me and we’ll meet you there after the case.”

“Okay,” Sam slowly walks out of the room. “I’ll, uh, see you then.”

Dean nods and the door closes. “Holy fuck.”

Benny pats Dean’s shoulder. “See? Wasn’t that hard. Now you just have to tell him you’re his brother and then that you are bisexual. Not too hard, cher.” 

Dean laughs. “Easy for you to say, vamp.”

Benny shoves Dean and they both laugh.


	7. Probably the worst chapter in this :/

**Summary for the Chapter:**

> I couldn’t get this chapter how I wanted. This is literally rewrite number 8 but Cas is up next chapter. 
> 
> Also, Sam’s not transphobic he’s just new to this. Don’t worry, he’ll have his own gender crisis later but Sam is he/they rights

December 14, 2007

“Hey, Charlie?”

“Yeah, Sam?” Charlie looks up from the Goblet of Fire book she is reading. 

“Do you know what’s up with Dean?” Sam leans forward on the chair next to the desk in the hotel room. They just finished a hunt and are going to leave in the morning to get back to Bobby’s place for Christmas. “He’s been hanging with Benny more than either of us, now. I was just wondering if you knew why or not.”

Charlie closes the book with a soft thud. “Sam…”

Sam nods. 

“It’s not my place to say.”

Sam sighs. “Does it have anything to do with me?”

Charlie throws her arms across her chest. “Sam, not to make you seem like a narcissist, but Dean does have a life outside of you. I don’t know much about his relationship with Benny, but I do know that they enjoy each other’s company. That’s all I can really ask for, you know?”

Sam holds his hands up in a surrendering position. “I’m just worried!”

“Uh huh,” Charlie raises an eyebrow. “Is this another start up to your argument against Benny or is this something deeper?”

“What are you talking about?” Sam’s brows furrowed. “Something deeper?”

“Ever since Dean told you he’s trans, you’ve been treating him with kids gloves.” 

“No!” Sam looks up to see Charlie’s disapproving stare. “I just think she should be careful around Benny, especially because he’s a vampire.”

“See! You called Dean a ‘she’ again!” Charlie stands up from the bed. “You never called Dean ‘she’ before he told you and now look at you! Dean has suffered so much for you-!” Charlie gasps. “Shit!”

“What does that mean, Charlie?” Sam stands up and grabs her arm. “What do you mean Dean’s suffered for me?”

“No, Dean will tell you on his own time.”

“Charlie,” Sam grabs her hands. “Please? I’m pretty sure Dean’s filled up his emotional fragility for the next year after he told me he’s trans.”

Charlie shakes her head and looks away. “Sam, it’s something very personal. The only reason I know about it is because he’s…”

“Your brother,” Sam sighs. “Fine. I’ll give him a few months. If he doesn’t tell me by, uh, let’s say my- my birthday then you’ll have to tell me.”

Charlie frowns. “Fine. I guess.”

Sam smiles. “Thanks, Charlie.”

Charlie falls onto her bed. “Dean’s going to hate me.”

January 24, 2008

“Happy Birthday, dear Dean!” Everyone sang. “Happy birthday to you!” 

Dean laughed before blowing out the candles. Sam, Bobby, and Charlie clap while Benny messes up Dean’s hair. 

“29!” Bobby says, letting out a low whistle. “Almost an old man like myself, huh?”

“Old?!” Dean laughs. “You’re a relic, Bobby.”

“You know,” Sam whispers to Charlie, while Bobby and Dean throw sassy insults at each other. “Dean shares the same birthday as my sister. He kinda looks like her, too.”

Charlie freezes for a second. “Oh? Wow, that’s, ha ha, that’s crazy.”

Sam furrows his brow before shaking his head. “Yeah, it’s, uh, it’s kind of weird but I think I can accept that she’s gone now. I think having Dean’s birthday pushes down the fact that her and Dean would be around the same age. It gives me something else to focus on instead of missing her.”

Charlie doesn’t know how to react. “Well that…that’s good. I’m going to go get, uh, napkins.”

Sam shakes his head again as he watches Charlie almost run to the kitchen. He looks back at Dean to see him and Benny staring at each other again. Bobby makes eye contact with Sam before gesturing to the cake. 

“It ain’t going to eat itself, idjit.”

May 1, 2008

“Sam!” Dean sprints into the room where Charlie and Sam are sleeping at 11:50pm. “Charlie! We gotta go. Now!”

Charlie recognizes the glint in Dean’s eyes and nods. As she shoves everything in sight in her bag, Sam asks, “What? Why?”

“Hellhounds are after me.” Dean grabs Charlie’s bag and runs to the two cars in the lot. 

“Charlie,” Sam turns to look at her. “What did he just say?”

“We’ll talk in the car, Sam.” Charlie grabs Sam’s keys from the nightstand. “If he’s right, we don’t have long until they’re here.”

Sam balks for a few moments before grabbing his things and running after Charlie. 

“...and take Sam down to Bobby’s place. I’m taking Benny with me back to Kansas.”

“Are you sure you want to go back there?” Charlie places a hand on Dean’s shoulder. “John is there.”

“Ain’t no time like now to see that bastard's face.” Dean smiles and looks over to Sam. “Heya, Sammy. You and Charlie are going to Bobby’s to load up while Benny and I try to run the bitch around.”

Sam squints but decides not to mention anything that was said between the Bradbury’s. “Alright. But someone has to explain why this is happening soon.”

“You got it, Sam.” Charlie spins the keys around her fingers before opening the driver’s door. “I’m driving, then, Chewie.”

Sam sighs. “Fine. But explain, please.”

As they drive off, Benny rests a hand on Dean’s knee. “We’re not losing it, huh, cher?”

“I’m not losing the hound, Ben.” Dean doesn’t look at Benny, continuing to stare out the front window. “I’m dropping you off in the next city and I’ll try to gank it back in Lawrence. Who knows,” Dean finally looks at Benny, tears forming in his eyes. “Maybe I can take him with me.”

Benny frowns. “Dean, I’m going with you.”

“No,” Dean slaps the steering wheel, causing Benny to flinch with how loud it is. “You’re not! You’re going to get somewhere safe and take care of Sammy for me.”

“You know I can’t do that,” Benny looks down at his hands, crinkling an old receipt he found in his pocket. “I can’t let you give up.”

“It’s not ‘giving up,’” Dean pulls the car over before pressing his forehead into the steering wheel. “It’s...it’s needed. It’s my fucking job, Benny.”

Benny crumples the receipt in a fist and looks at the back of Dean’s head. “It’s a job you never asked for, given to you by a sack of shit. John ain’t here to tell you to look out for him. If he was here, what would he have said when he learned about your deal, huh? Good job?”

“Son of a bitch!” Dean hits the dashboard before looking at Benny, rage in his eyes. “Shut up about my dad! You have no right! None! You don’t know how it was growing up and making sure Sam had everything he wanted while I was kicked down every time I asked why I had to do something!”

“Dean-“

“No! You listen to me, Benjamin Lafitte!”  
Dean grips the steering wheel briefly before covering his face with his hands. “You don’t have the right to tell me that making that demon deal was a mistake. If I had the chance to do it again, I would. No hesitation. He’s my brother, Ben. He’s like my own kid, with how much I raised him.”

Benny is silent in the passenger seat. He folds one leg on the Impala’s bench and stretches an arm towards Dean. Dean takes Benny’s hand in his before continuing. 

“John might not do the same to bring Sam back, but John isn’t his father. I know you hate my choice, but c’mon, Benny. I would do anything for Sam.”

“Sam doesn’t even know who you are,” Benny frowns slightly. “You still haven’t told him.”

“He’ll know when I’m gone.” Dean turns back to the road and starts driving again, keeping a hand in Benny’s. “I’ve been trying to read up on the hell dogs the past few days. ‘M pretty sure they’re weaker when hit with iron. Not sure.”

“We’ll be sure to stock up and test it, then, cher.”

Dean smirks before accelerating the car down the empty road. 

“So we’re really going to let Dean fend for himself against- what again?” Sam looks up at Charlie. “Hellhounds? I thought only people who made demon deals get chased down by them.”

“The thing is, Sam,” Charlie tries not to look at him while she drives towards Bobby’s place. “Dean did make a deal.”

“For what?!” Sam is baffled. That’s the one thing Dean always warned him not to do. 

“For you, bitch.” Charlie sighs. “It’s not easy to say this, but that hunt a year ago actually killed you. Dean made a deal to bring you back, but instead of ten years, he got only one. It was a big request, i guess. He’d do anything for you, Sam. It’s his job.”

“But why?” 

“Dean is…” Charlie pauses. She really needs to let Dean tell the rest of it, but she’ll at least hint to Sam about who Dean is to him. “Well, he’s not actually my biological brother.”

Sam is speechless. “So- so what? You’ve been lying to me- to everyone this whole time?”

“I met him in Ontario after I was kicked out of my parents house for being gay. Turns out, being trans was the least of his problems. He faked his death and ran away from home because of shit out of his control.”

Sam looks down. He never knew Dean ran from him. He just assumed that Dean was making his parents proud. “What happened?”

“I can’t say much,”Charlie glances at Sam. “He hasn’t told me every detail, yet but it was bad. Like “I’m surprised he hasn’t killed himself” type of bad.”

“Shit…”

“Yeah,” Charlie lets out a sharp breath in amusement. “And I met him there and we’ve never been separated since. He told me about hunting and monsters; showed me this journal he wrote for his dad that had everything in it a hunter could ask for.”

“My dad had a similar thing,” Sam remembers how John ransacked the burned motel and car for the Winchester Journal he was known for. He went crazy trying to find it and was never the same suave guy on hunts ever since. “He lost it in a fire with my sister. She got killed by a demon for laughs.”

Charlie frowns. “I’m sorry to hear that.”

“It’s, uh, it’s fine.” Sam sniffs. “She was like a mom to me. Practically raised me herself while my dad hunted for the demon who killed my biological mom.”

“Why don’t you tell me about her?” Charlie wants to hear stories of young Dean without the self-mutilation of his feelings. “You don’t mention her a lot.”

“She was the best.” Sam looks out the window so Charlie doesn’t have to see him tear up. “She looked exactly like my mom, according to dad. I remember how she always helped me with homework and cooked meals for me after school. She always wore her hair in a braid. She also protected me from dad whenever he tried to teach me to hunt. I remember one time she was sick and stayed in her room for a week and I learned how to shoot with my dad. I was about 6 at the time. I hated it.”

“Your dad sounds like a dick.” 

Sam laughs. “He was awful. I remember when I was around fifteen, he gave me my own gun for Christmas. I could tell Mary hated him for that but she volunteered to go with John on the hunt he was trying to take me on. She always volunteered in my place. I don’t know why because she always came back beaten to a pulp by the monsters.”

Charlie nods. The only monster beating Dean was John himself but she wasn’t about to tell that to Sam. “She sounds like a saint.”

“I’m sure she’s one now.” Sam laughs. “Every time my dad forced her to go to some school dance, she would leave early. All of her dates were pretty much hand picked by either dad or Uncle Bobby. She hated wearing the dresses and make up, but I caught her a couple times with her best friend, Cassie, twirling around in them after the dance was over. I’ll always remember how happy she was then.”

Charlie turns onto Bobby’s street. “She sounds like a great sister. I’m sure she loves you very much.”

“I like to think she sent Jess to me.” 

Charlie is silent. Sam never brings up Jessica anymore and she doesn’t want to spook him off his emotional dump right now. 

“It’s just…” Sam sighs and looks out at the passing trees. “Jess was the best thing to happen to me, especially after Mary died. She left me a college fund after she died, you know. Mary always hated that I wanted to go but I always thought she was jealous because she didn’t go to college. Everyone thought she would but then she dropped out of high school a few months before graduation and got a job. She got me out to California where I met Jessica and I can never thank her for that.” 

Charlie parks the car and turns off the ignition. Sam sniffles silently while Charlie contemplates her next words. 

“Sam, if I were to tell you that Dean knows what happened to Mary, what would you say?”

Sam snaps his head towards her. “What?” 

Charlie purses her lips. “Dean is...well, he knows what happened to her. And if we can get Bobby to give us some iron weapons, I’m sure Dean will explain it to you.”

As Charlie steps out of the car, Sam calls her name. 

“Charlie!”

“Come on, Sam,” Charlieleans down to look at him in the passenger seat. “If we don’t save Dean, you’ll probably never get to reunite with your sister.”

Sam jumps out of the car, hitting his forehead on the door. “What are we waiting for?”

Dean turns off the engine and sits for a moment in the driveway of the newly built Winchester home. After the fire, the remains of the house stayed there for about ten years before some west coast family bought it and remodeled it. It has a for sale sign in the yard and Dean hopes it stays that way for a while. 

“Are you ready, brother?” Benny asks, cocking a shotgun. 

Dean laughs. “After that bj I gave you yesterday, you’re really calling me brother? I thought you were from Louisiana not Alabama.”

“Fuck off,” Benny laughs. “Let’s fry these dogs up so I can show you what a real Cajun Lovin’ looks like, Dorothy.”

Dean smiles wider before stepping out of the car. “You gonna show me your yellow brick road, then, huh?” 

Benny laughs before getting out of the car. Benny’s hoping for a quick and easy slice and dice with these hounds. He can’t wait to just spend the weekend with Dean in the sun back in his house in Louisiana. He’ll ask Dean to marry him- hell, move in with him at least- then. He’s patient. He can wait another lifetime for Dean Winchester. 

Dean and Benny are running into the hallway when a hound corners them. 

“Dean?” Benny says softly. “When I say run, you run. No looking back- no hesitations, okay?”

“What?!” 

“Run!” Benny launches himself where he can see the dusty paw prints end and yells when he is bit. Dean freezes for a second before taking off past the hounds. He can hear Benny’s screams along with the hellhounds snarling and barking. Benny is able to take down one of the three hounds after Dean before he’s bit in the neck. He’s almost fully decapitated, gasping for breath as the hounds move off him and slowly walk down the hallway to the back door. 

A tear falls down his cheek as he hears Dean yell for Sam and Charlie before he passes out. 

Dean sprints outside the house and expects to have a clear path to his Baby only to see Sam’s car in the driveway. 

“Sam?” Dean looks around while jogging to the dark red 1979 Thunderbird. “Sammy?!”

“Shit!”

Dean turns back to the house. He can hear Charlie scream again and runs back inside. “Charlie? Sam?”

“Bedroom!” Sam yells. 

Dean looks around the front area of the house to see the kitchen to his left. He raids he cabinets looking for some type of powder he could probably throw on the fucking beasts so they’ll be easier to see. Just as his hand wraps around a bag of powdered sugar, a deep snarl comes from across the room. Dean turns to look at the dog’s smoldering black eyes. 

“Easy there, Lassie.” Dean slowly reaches behind himself, grabbing a small can of something. “I’m right here.”

Dean throws what turns out to be a salt shaker at the hellhound and watches as it whimpers at the smoke rising from where the salt touched it. He’ll have to add that to the journal if he gets out of this. 

Dean vaults over the hound as another one pokes its head out of the bedroom. Dean throws the bag of powdered sugar at it before kicking it out of his way. 

“Sam! Charlie!” Dean makes his way around the other side of the bed to check them both for injuries. “The hell are you guys doing here?”

“Sam didn’t want to leave you to fend for yourself.” Charlie says, wincing as Dean pressed into a bruise on her arm. “I told him about the deal.”

“Charles-“

“He deserves to know, Dean!”

“Guys!” 

They both turn to look at where Sam is pointing and Dean sees both hounds standing a few feet away. Dean looks at the two of them. 

“Can you guys see them?”

“Them?” Sam asks. “I can see one set of footprints because of that flour you threw at it.”

“How many are there?” Charlie asks. 

“Two,” Dean swallows before shifting his feet. “Benny got the third one, I guess.”

Dean can see the hounds focusing on Sam and Charlie. He lost Benny, he won’t lose them, too. 

“On the count of three, you two get the hell out of dodge. My keys are still in Baby.”

“What?” Sam balks. “We won’t leave you here!”

“One,” Dean takes a deep breath. “Two…”

Charlie pushes Sam over the bed as Dean yells ‘three!’ and jumps at the two hounds. Once the two of them are out of the room, Dean turns to follow, the hounds biting at his heels and leaving gushing wounds. 

“Hey, Sam!” Dean calls out. “Next time you see dad, tell him I said ‘I’ll see you in hell,’ alright?”

The hellhound turns to look at Dean. Sam is confused while Charlie nods at Dean, taking Sam’s arm. “What does that mean?”

Dean opens the door to the bedroom. “I’m your sister, Sam. Now get out of here!”

The hellhound starts to run at them and Charlie pulls Sam out the door to the backyard. 

“Mary?!”

Dean throws a chair at the back door to close it. “Give ‘em hell for me!”

“Mary!” Sam yells, pushing Charlie away from him as he runs back inside. 

Dean spots Benny’s prone body in the entrance of the bedroom. The two hellhounds stand a few feet away from him on the other side of the room. Dean bends down to see a piece of Benny’s neck missing. Benny opens his eyes. 

“Dean…”

“It’s okay, Ben.” Dean looks up at the hounds for a second before pulling out a long blade from his inside jacket pocket. “I’ll...I’ll end it.”

Benny smiles and closes his eyes before Dean slices through the rest of his neck. The hounds take that opportunity to lunge at him and before he can process their movement, he can feel the dogs pull apart every muscle from his chest and stomach. He screams until he’s hoarse and the beasts start dragging his body away from Benny’s. Dean tries to claw his way back, to see Benny’s face one last time, but the hounds yank on his leg so hard, some of the muscle strips off his bone. As the hellhounds feast on his body, he feels an odd sense of relief wash over him. 

‘At least my boobs are gone now,’ is his last thought before he wakes up chained to a table.


End file.
